Chuck vs The Story
by Charahfan44
Summary: When Chuck's daughter wants to hear the story of her parents meeting, he tells her, but it comes with a twist. He changes the names of the women, making his daughter guess which one her mother is. Based on Definitely, Maybe. AU. I do not own Chuck!
1. Chapter 1

**A/N:** **Hi everyone! So, I know I always start new stories before I finish any of the ones I'm already writing, but I just can't keep my ideas inside. I have a need to let them out before I burst! I promise I will finish my other stories, I'm not going anywhere. This one is based on the movie _Definitely, Maybe_ starring Abigail Breslin and Ryan Reynolds. It's one of my absolute favorites, and I thought it would make for a fun Chuck fanfic! I'll try and throw in some hints here and there, but it's really a guessing game for all of you. Let's see who can figure out the mystery first!**

 **-Charahfan44**

* * *

 **PRESENT DAY**

I don't often ask my parents for anything, especially now since they are going through a separation. They told me a few months ago, and we've all been trying to adjust since then. Every two weeks, I switch off to another parent. The first two weeks of the month I spend with my mom, and the last two with my dad. It's not exactly the dream scenario, but I'm glad to have them both. Today, it was my dad's turn to pick me up from school, starting our two weeks together. He was as chipper as usual, which always lightened my mood.

"Hey, kiddo." He smiled as I opened the car door.

"Hi, dad." I smiled back, jumping in.

"How was school?"

"The same as it always is." I buckled myself in. "I'd really like to be in high school already." I added.

"One more year. It'll go by fast, trust me." He replied. I had just started my last year at the junior high, and I wasn't exactly loving the eighth grade.

"You always say that, and then time seems to slow down." I sighed.

"Trust me, I'm usually right." He joked. "How was your two weeks with mom?" He asked. At first, I didn't mind when they each asked me about each other, but now it was starting to get annoying. Every time I switched off, they would sneak in a question about the other.

"Fine." I responded. I had decided to start keeping my answers short and sweet. Maybe this way, they'd start talking again.

"Well that's better than bad." He laughed. "What do you want for dinner tonight? I haven't had time to go to the store this week, so we'll be ordering in."

"What do you feel like?" I hated making decisions, which is something I didn't develop from either parent.

"Let's go with Chinese."

"Sounds like a plan." The rest of the drive was silent in conversation. Dad and I liked to listen to the radio together, humming or singing along with the melody. When I was younger, we'd put on little concerts in our living room, mom video taping every single one. Little did I know, they'd use the videos to embarrass me at an older age. It didn't take us too long to get home, as dad's new apartment was only a few blocks from the school.

"Get started on your homework, and I'll call in to Bamboo Dragon." He said, putting his keys and work bag on the counter of the small kitchen.

"Aye aye, captain." I replied, sitting down at the living room table. I hated how tiny his apartment was, but knew that he was still holding out hope to move back home with mom and I. Before they split, they had been fighting a lot. I wouldn't be able to sleep because they're voices were so loud. At one point, I had to go into their room and break up the shouting match. I think it was that point in time that they realized they needed a break from each other. I stared at my math homework, unable to make sense of the numbers and symbols. I wasn't great with math, and my crowded mind wasn't helping.

"What are you working on?" Dad's voice loomed over my shoulder.

"Algebra." I said.

"I loved algebra when I was in school." He said excitedly.

"Makes one of us." I groaned.

"Need some help?"

"Please." I replied. He sat down next to me, and helped me with each problem I didn't understand. Our food came almost forty five minutes later, and we ate it like we had never eaten anything in our lives. He always made sure I was in bed by ten o'clock.

"You good?" He asked from the doorway.

"Yes." I said with a hint of annoyance. I hated it when he tried tucking me in like a child.

"Okay, okay," He put his hands up in surrender, "Just checking." He turned to leave.

"Hey, dad?"

"Yeah?" He turned back to me.

"Can I ask you a question?"

"Always." He smiled.

"Can I hear the story about you and mom?"

"What story?"

"The whole story. Everything that led up to this moment." I held his gaze.

"What prompted this?"

"I don't know, I just still don't understand why you guys aren't together." I looked away briefly.

"Even with a story, I won't understand it myself." He admitted. "But I can tell you if you really want to know."

"Okay." I felt my face light up. "Did you ever date anyone else?"

"What?" He laughed nervously.

"You know, was there anyone else before mom?"

"Sure, I had other girlfriends." He shrugged, coming over to sit at the edge of my bed. "Tell you what, I'll tell you the story of my three most serious girlfriends, and you have to guess which one is your mom."

"But I know mom's name." I laughed.

"Okay, I'll change the names." He said.

"Deal." We shook on it playfully, and I settled into my bed comfortably.

"Okay, let's start with the summer of two thousand."

* * *

 **August 24th, 2000**

 _Chuck Bartowski was one of a kind in every way. He was the nicest guy around, and most people knew who he was. His best friend, Bryce Larkin, was considered the big man on campus, but he made sure Chuck had some popularity as well. Today was the first day of sophomore year at Harvard, and everyone was already bustling around the campus. Chuck, being his usual self, was busy looking down at his class schedule, when he bumped into someone._

 _"Watch it!" The voice shouted, obviously upset._

 _"Sorry, I didn't notice you." He mumbled, picking up the book the stranger had dropped._

 _"Obviously."_

 _"I really am sorr-" He stopped short, looking up at the person. She was the most beautiful woman he had ever seen. Something about er struck him hard, causing him to lose any word he had in his mind._

 _"Did you hit your head or something?" She asked snottily._

 _"Uh, no." He handed her the books. "I just...you..."_

 _"Maybe you should put some English classes on your list." She rolled her eyes._

 _"Yo, Chuck!" Bryce's voice sounded from behind. "We've got to go."_

 _"Bryce Larkin." The girl looked in the direction of Chuck's best friend._

 _"You know Bryce?" Chuck asked._

 _"I know of him." She replied._

 _"Well hello there." Bryce put on his charm as he approached the two. "Are you new here?"_

 _"How'd you know?" She asked._

 _"I definitely would've remembered seeing someone as beautiful as you." Bryce replied, flashing his famous mega-watt smile._

 _"I'm Kate." She reached her hand out for his._

 _"Kate. I like that." He gladly shook her hand back. "Sorry to interrupt this little meeting, but Chuck and I have to go."_

 _"I'm sure we'll see each other around." Kate smiled._

 _"I'm betting on it." Bryce winked. "Catch you later, Kate." Bryce watched as she walked away, admiring her beauty._

 _"I ran into her." Chuck winced. "Literally."_

 _"Damn, a girl like that doesn't just waltz into your life for nothing." Bryce kept his eyes on Kate. "But hey, we have a frat party to host tonight."_

 _"Really?" Chuck groaned. "I told you, I'm not into the whole party thing."_

 _"It'll be fun, I promise."_

 _"Why didn't you invite Kate?" Chuck asked, wanting to see her again._

 _"I definitely want to wine and dine her, you feel me?"_

 _"Sure." Chuck shrugged._

 _"It's okay, Chucky, we'll find you a girl tonight."_

 _"How about I stay single and focus on school?"_

 _"Chuck, college is the time for bad choices. You should let yourself have some fun."_

 _"Maybe someday." The two walked to their dorm room, and settled in for the next few hours. Bryce was constantly checking himself out in the mirror, but Chuck didn't mind. At the end of the day, Bryce still played video games and ate junk food, and that's all Chuck could hope for._

 _"Dude, we have to leave in like, twenty minutes." Bryce had finished getting ready by ten o'clock that evening._

 _"I think I'm coming down with the flu." Chuck forced a cough._

 _"Get your party clothes on, you're going." Bryce said. He always forced Chuck to leave the room and have a good time. They got to the frat house in less than ten minutes, Bryce lighting up the place as he walked in. "The party has arrived!" He threw his hands in the air, causing everyone to erupt with cheers._

 _"Nice place you got here." Chuck jokingly said to the bobcat statue next to the doorway._

 _"Dude, who are you talking to?" One of the frat boys looked at him with disgust._

 _"Uh, myself." Chuck scratched the back of his head before following Bryce to the drink table._

 _"What're you having, Chuck?" Bryce asked._

 _"Water is fine."_

 _"Rum and coke it is."_

 _"Seriously, I don't need a drink."_

 _"Seriously, yes you do." Bryce handed him a cup. "Drink up, science boy."_

 _"Fine. But just this one." Chuck sipped on his drink lightly, getting abandoned by Bryce almost immediately. Chuck was sure he was off flirting with a beautiful woman, because that's what he did best. He made his way out to the balcony, already looking for fresh air._

 _"Looks like we're the losers stuck out here with no one." A familiar voice said behind him. He whirled around to see Kate holding a drink in her hand. "You." She recognized him in a heartbeat._

 _"This isn't awkward." He said sarcastically._

 _"There's no going back now." She stood beside him, peering over the bars on the edge._

 _"I didn't really take you for a party girl."_

 _"You don't know me at all."_

 _"True." He looked down below. "I've just been yelled at by you."_

 _"Whoa, wait a minute." She looked at him. "I did not yell. I merely raised my voice because you ran straight into me."_

 _"Maybe if you had been looking, you would've avoided me." He sassed back._

 _"You're basically a wall, no one can avoid you." She laughed._

 _"Wow, a smile?" He laughed back. "What a rare surprise."_

 _"I'm not a total bitch. Just a tiny one." She took a drink from her cup. "So, you're friends with Bryce?" There it was. The one question that all women asked him._

 _"Yeah."_

 _"Is he seeing anyone?"_

 _"He's seeing everyone." Chuck mumbled._

 _"You think you could put in a good word?" She asked._

 _"I'd love to."_

 _"Thanks, uh..." She trailed, forgetting his name._

 _"Chuck." He said flatly._

 _"Right, Chuck." She looked at him guiltily. "I should probably get back in there. See you around?"_

 _"See you around."_

* * *

 **PRESENT DAY**

I was falling asleep as dad told me the story, but I desperately wanted to hear more.

"What?" I raised my voice. "She used you to get Uncle Bryce?" I asked.

"I wouldn't say 'used'." He replied with a laugh. "She just didn't have feelings for me yet."

"I can't believe you let this woman become a serious girlfriend." I shook my head. "She definitely doesn't sound like mom."

"You never know." He said slyly.

"So this Kate lady _is_ mom?"

"I didn't say that." He kept his mysterious tone. "I said you never know."

"Okay, this so isn't fair."

"You shook on it." He joked.

"Yeah, but I didn't shake on you confusing me." I pouted.

"Just wait until I tell you the whole thing, and then you can tell me who you think your mom is."

"What happened after the party?" I asked.

"We'll have to hear about it tomorrow." He smiled, kissing my forehead softly before getting up to leave.

"You can't leave it like that!" I whined.

"Sure I can." He winked. "Get some sleep." He turned my light off, shutting the door softly. That night, I couldn't sleep at all. He had only told me a tiny portion of his story, and yet I had thousands of theories swirling through my mind. I wanted to hear the next part so badly, only because I wanted to hear about the other two. At eleven o'clock, I looked to my phone, and dialed my mom's number.

"What are you still doing up?" She didn't sound happy that I was awake.

"Can't sleep." I kept my answer short.

"You okay?" She asked.

"Yeah, I'm just thinking about stuff."

"What kind of stuff?"

"I really wish I didn't have to stay here." I sighed.

"I know." Her reply seemed sad. "But, you need time with your dad too."

"I didn't mean here with dad, I meant here period. We should both be at home."

"We've talked about this."

"I know. It's still hard."

"It will get easier."

"Doesn't seem like it."

"You should go to bed, okay? Enjoy the weekend with your dad." She changed subjects.

"Okay."

"I love you." I could hear the empathetic tone in her voice. She knew that their decision affected me heavily, but she wouldn't change her mind.

"Love you too." I said back. I hung up, finally feeling tired. I wasn't the type of person to ever realize when I fell asleep, so it always felt weird waking up. When I woke up the next morning, I was on my dad's case before he even had time to think.

"What happened next?" I asked, watching him make omelets.

"Can we at least eat breakfast first?"

"You said you'd tell me more tomorrow, and tomorrow is now." I sat at the dining room table in front of the kitchen area, unable to hide my excitement.

"You are my kid, aren't you?" He laughed, shaking his head.

"Obviously you and Kate dated, or you wouldn't be telling me about her. I want to hear how you guys got together!"

"It took a long time for us to get there."

"Good thing we have lots of time."

"Fine," He brought a finished omelet over to me, "I'll continue."

"Great." I smiled. "So, after the party." I reminded him.

"Right. After the party."

* * *

 **October 3rd, 2000**

 _Only a few months had passed since Chuck and Bryce had first met Kate, and now they spent every moment together. Bryce and Kate had obviously developed an intimate connection, one Chuck could've only dreamed of. He spent most of his off time studying in the library, mostly due to the fact that he didn't want to see his crush and his best friend all over each other._

 _"Thought I'd find you here." Kate's voice caused him to look up from his anatomy book._

 _"Oh, hey." He looked back down almost immediately._

 _"What a greeting." She joked. "You busy?"_

 _"Sorry, I just can't get a bad score on this test." He sighed._

 _"Want some help? I actually understand quite a bit." She sat across from him at the table._

 _"Right, I forgot we have the same class."_

 _"Forgot? We sit next to each other." She laughed. "You okay?"_

 _"I'm fine, just stressed."_

 _"Bryce said you'd been acting weird the past few weeks."_

 _"Yeah."_

 _"Maybe what you need is some time away from school." She said._

 _"What do you mean?"_

 _"You never get away from campus, maybe you should." She shrugged._

 _"My entire life has been about getting into this school, Kate. I can't slack off now." He replied._

 _"I'm not saying you need to slack off, all I'm saying is that maybe you deserve a night off."_

 _"Oh yeah? And where do you suggest I go?"_

 _"There's a really fun mini golf course that Bryce and I were planning on going to tomorrow. You should come!" She smiled._

 _"What a fun night that sounds like." Chuck said facetiously._

 _"You know, I have a friend that totally loves guys like you." She added. "I think you'd like her."_

 _"I don't know..."_

 _"Please? I want you to come. Let me set you up, I promise you'll have a good time."_

 _"Fine." He looked at her, feeling a smile form on his face, mimicking hers._

 _"Good. Tomorrow night, at six." She got up just as quickly as she had sat down. "Oh, uh, would you mind hanging out here for a bit? Bryce and I will be in your room and I don't want you to walk in on...anything." She added the last part sheepishly._

 _"Sure, no problem." Chuck pretended to be cool._

 _"Thanks, Chuck, you're a really good friend." She smiled once more before leaving the library. Chuck sighed, looking back at his anatomy textbook. He stayed there for a few hours, not wanting to interrupt anything that may have been happening back in his room. He got home around seven, and was relieved to find the room empty. The next day went by quickly, and he passed his anatomy test with a ninety-one percent. Kate came over before the double date, checking in on Chuck._

 _"I don't think I can do this." He said, struggling to pick out a shirt._

 _"Chuck, you're going to be fine." She laughed. "But not if you wear that." She gave his ratty Harvard shirt a disapproving look._

 _"Help." He begged. Kate bee lined for his closet, picking out anything she thought would pass for a date._

 _"Here, put this one on." She handed him a dark blue button up._

 _"If I look like an idiot in front of this stranger tonight, I'm not going to talk to you ever again." He said, putting on the shirt._

 _"That's definitely the one." Kate smiled, watching him check himself over in the mirror._

 _"We ready to go?" Bryce entered, holding a six pack._

 _"Doesn't he look good?" Kate asked her boyfriend._

 _"Uh, guys don't really tell each other how cute they look." He popped open a beer, kissing Kate quickly._

 _"I think he looks great." She nodded._

 _"Thanks." Chuck smiled. There was a sudden knock on the door, and Kate answered it. A woman walked in, looking confident and completely sure of herself. She was tall, but not as tall as Chuck._

 _"Julia, this is Chuck." Kate led her friend into the main part of the room. "Chuck, this is Julia."_

 _"Hi." He stuck out his hand._

 _"You're cute." Julia replied, shaking it._

 _"Uh, thank you." He scratched the back of his head nervously._

 _"We should go." Bryce said. The four exited the room, Bryce and Kate walking hand in hand. Chuck couldn't help but imagine himself with Kate, doing all the couple-y things people did._

 _"It's okay, I won't say anything." Julia whispered._

 _"What?" He looked to her._

 _"I've seen you around, looking at her like you are right now."_

 _"I don't-"_

 _"Oh please, Chuck. You like her."_

 _"She's my friend."_

 _"I'll help make you look good tonight, don't worry. Maybe we'll even make her a little jealous." She grabbed his hand and intertwined her fingers with his. This night was going to be interesting, and this was only the beginning._


	2. Chapter 2

**A/N: Hi guys! I'm absolutely loving the reviews on this story already. Hearing some of your theories makes this a thousand times more fun! I am going to say that no one is even close yet, but that's because these first few chapters are only the first piece of the puzzle. I'm rewatching Chuck from the beginning right now, which I haven't done all the way through in a few years. As always, thanks for reviewing, and thanks for reading!**

 **P.S. I haven't named the daughter yet because I haven't found a name I like. It doesn't have any significance to the story!**

 **-Charahfan44**

* * *

 **October 3rd, 2000**

 _The mini golf course was turning out exactly as Chuck had expected; awkward. He was trying his best to mesh well with Julia, and not focus too much on what Bryce and Kate were doing, but he wasn't having much luck. Bryce did his usual thing, wrapping his arms around her and pretending as though he really knew how to hold a golf club. Kate took the bait, allowing him to show his affection._

 _"Dude. You have got to get some balls." Julia said, watching Chuck._

 _"They're already together." He replied. "And he's Bryce Larkin. I'm no one."_

 _"Do you really believe that? I think there's more between you and Kate than you realize."_

 _"What do you mean?"_

 _"Here." Julia stepped in front of him, planting his feet firmly to the ground. "Put your hands around my waist." She instructed._

 _"What?"_

 _"Just do it." She gave a slight laugh._

 _"Okay." Chuck did as she said. "Now what?"_

 _"Kiss me."_

 _"Here?"_

 _"Bartowski, I'm giving you free reign to use me. You won't get another offer like this, trust me."_

 _"I don't want to use you."_

 _"That's why I'm letting you."_

 _"But-" His words were stopped by Julia's lips. What started out as a simple kiss evolved into a full on make out between the two. As nervous as Chuck was to be with this incredibly beautiful woman in the middle of a putt-putt gold course, he couldn't help but live in the moment. They separated after about a minute, both unsure of what to say._

 _"Damn, Chuck." Julia finally said._

 _"I may have some surprises hidden up my sleeve." He said slyly._

 _"You don't say." She smiled, turning around to move on to the next hole. "It worked, by the way."_

 _"What did?"_

 _"She saw the whole thing." Julia stated. Chuck looked ahead, catching Kate's eye for a split second. She looked at him somewhat disapprovingly, and Chuck noticed a flicker of jealousy. Julia reached for his hand, pulling him forward. "Let's go, champ."_

 _"I don't know if that's the best word to describe me." He said playfully._

 _"Should I call you frenchy, then?" She raised an eyebrow._

 _"We can stick with champ." He nodded in embarrassment._

 _"There you guys are. I thought we were going to have to come and pry you apart." Bryce clapped Chuck on the back. "Good going, man."_

 _"He's better than you described, Kate." Julia cuddled up to Chuck. "Thanks for setting us up."_

 _"No problem." Kate nodded shortly._

 _"Do you guys mind if we get out of here?" Julia asked._

 _"What?" Chuck and Kate asked in unison._

 _"I'd like to go back to my place." Julia rubbed Chuck's arm softly._

 _"Of course not, go have some fun." Bryce winked._

 _"Thanks." Julia pulled Chuck away. "I'll have him home tomorrow."_

 _"Where are we really going?" Chuck asked as they walked away._

 _"My place." Julia replied._

 _"Uh, I don't know if I'm ready for that level of espionage."_

 _"Relax, Chuck. We don't have to do anything other than hang out."_

 _"Is this all really a good idea? Kate looked mad."_

 _"That's on her, not you. She set us up. Besides, if she's mad, it's because she's jealous. She need to figure out what she really wants, it's not fair for you to keep pining after her if she likes you too."_

 _"I guess you're right."_

 _"That's how it normally goes." She laughed. "You'll learn, Chucky. You and I are going to be great friends."_

* * *

 **PRESENT DAY**

I stared at my dad as we entered the produce section of our local grocery store. I was starting to become so invested in this story that sometimes I forgot just what exactly he was saying.

"So she wanted to sleep with you to get back at Kate?" I asked, grossed out.

"I probably should've left that part out." He looked down at the tomatoes in front of him.

"You didn't do anything with her did you?" My tone was serious.

"Of course not, who do you think I am?" He replied.

"I don't know. I definitely didn't think you'd use a girl to make another one jealous." I frowned.

"Maybe telling you all of this isn't such a good idea."

"You've already started, you can't stop now!" I whined. "Plus, we shook on it."

"That we did." He laughed.

"So did you and Julia end up together?"

"No, actually. After that night I never really saw her again."

"You didn't?"

"She wasn't really my type." He laughed again. "Trust me."

"Was Kate jealous?"

"I think so."

"You don't know?"

"Not really. We kind of lost touch after that."

"What do you mean? She was still dating Bryce, wasn't she?"

"For a little while, yeah. But they didn't stay together."

"Why?"

"Your Uncle Bryce is not a one woman kind of guy." Dad explained. "It was a miracle tat he stayed with her as long as he did."

"When they broke up, did you swoop in and tell her how you felt?"

"No." He admitted.

"You chicken!" I yelled, causing people to look over. "Sorry." I put my hand over my mouth.

"Feelings are harder to deal with than you realize. Not everything is like the movies you watch." He said. "Real life has a way of repeatedly kicking you down, and it doesn't usually help you get back up."

"Well obviously you guys got together at some point, or else she wouldn't be in the story."

"You are correct."

"So how did it happen?"

"Patience, young grasshopper." He smiled. "You'll have to wait until we reach that part in the story."

"When will that be?" I asked.

"When I tell you more."

"The ride home?"

"Sure." He said with a grin. I basically rushed him out of the store, wanting to hear the next part of the story as quickly as possible. I got into the passenger side of the car, and looked at him expectantly.

"Alright, what happened next?" My eyes were wide with curiosity.

"I think I failed a math test the next day." He joked.

"Dad!"

"Okay, okay. Let's jump ahead just a bit, or we'll never finish."

* * *

 **December 20th, 2000**

 _With Halloween and Thanksgiving done and over, everyone on campus was looking forward to Christmas. Chuck was happy to go home, especially to see his best friend, Morgan. He tried keeping in touch with his family and friends back home as much a possible, but it was hard to do with his class load._

 _"Have a good time back home, Chuck." Bryce had a back pack and suitcase in each hand._

 _"Yeah, you too." They shared a "bro hug" before Bryce left the room. Chuck's flight was departing from Boston Logan International Airport in a few hours, but he still had plenty of time as it was only about twenty minutes from campus. He wanted to get a little more time in at the library before he left for the break, especially because he knew that the work load would increase when school started again. He bundled up in a sweatshirt, winter coat, jeans, long wool socks that his mother had sent, and his usual Chuck Taylor's. He shivered as he made his way through the library doors, feeling the warmth of the room almost immediately. He grabbed a book on chemistry, and sat down to read._

 _"This is how you're starting your vacation?" A familiar voice asked sarcastically. Chuck looked up to see Kate standing in front of him._

 _"You're in here, too." He replied, smiling his famous smile._

 _"I'm returning some things before I get fined," She pointed at his book, "You're actually working."_

 _"I guess you got me there." He laughed. "How've you been?"_

 _"Pretty good. Just busy with school, you know how it is."_

 _"That I do." He said. "It's been a while."_

 _"Yeah." She looked down. "I've been meaning to call you."_

 _"You don't have to lie to save my ego." He joked._

 _"Just because Bryce and I aren't together anymore, doesn't mean you and I can't still be friends."_

 _"I could've just as easily called you."_

 _"True." She allowed herself to smile. "You aren't staying on campus over break, are you?"_

 _"No, I leave in a few hours."_

 _"What a coincidence, so do I." She kept her smile. "We could probably split a taxi, it would be cheaper."_

 _"You're pretty smart, aren't you?"_

 _"You forgot?" She smirked._

 _"No, definitely not." He looked at her the way he used to, causing a moment of weirdness between the two. They looked away from each other, both laughing nervously at the awkward tension._

 _"I guess I can wait for you." She feigned annoyance to break the silence._

 _"I won't be here very long." They spent another thirty minutes in the library, mostly sitting in silence, glancing at each other every few minutes or so. It didn't take long for them to grab a taxi and get to the airport, especially because traffic was unusually clear. "Thanks." Chuck handed the cabbie some money._

 _"I thought we said we'd split it?" Kate asked._

 _"It wasn't that much." He replied. "It's fine."_

 _"What airline are you with?" Kate asked as they waked through the main doors of the airport, their luggage in tow._

 _"Uh, American. You?"_

 _"United."_

 _"So I guess this is where we part?"_

 _"I guess so." They stood facing each other, unsure of how to say goodbye. "We'll see each other in a month." Kate shrugged._

 _"Yeah, not a long time at all." Chuck agreed._

 _"See you later, then." She smiled._

 _"Later." He turned to leave, regretting the weird goodbye. "Kate?" He turned back around._

 _"Yeah?"_

 _"Call me when you get home?" He asked. "You know, just so we can talk about our flight experiences."_

 _"I will." She nodded before walking away. Chuck couldn't wait to hear from her._

* * *

 **December 25th, 2000**

 _Chuck had only been home a few days, but he already felt as though something was missing. He loved spending time with his family, and he cherished every moment. Going to a school so far away had really made him miss home. His sister, Ellie, stayed close to home, attending UCLA. This year, she brought her boyfriend home with her. She was in her final year, studying to become a surgeon._

 _"So, sis, how's school?" Chuck asked, the two of them sitting in front of the Christmas tree in the living room._

 _"Good. I'm sure you know how tiring it can be." She sipped her eggnog._

 _"Definitely." He mirrored her. "Devon seems like a good guy." Chuck peered around the corner to the kitchen area, watching Ellie's boyfriend help his parents with breakfast._

 _"He is." She smiled. "What about you? Have anyone special back at Harvard?"_

 _"Not really." He tried to keep a straight face, but failed._

 _"Charles Irving Bartowski, you spill the beans right this second!" She smacked him playfully._

 _"There is this one girl..." he trailed._

 _"Tell me everything."_

 _"There isn't much to tell. She dated Bryce for a few months and when they broke up, we stopped talking."_

 _"So ask her out." Ellie suggested. "Girls like guys who make the first move."_

 _"She doesn't like me like that, El."_

 _"She's said that?"_

 _"Well, no."_

 _"Okay then." She said firmly. "Chuck, you're a catch. I'm not just saying that because you're my brother."_

 _"You're obligated to tell me I'm awesome, it's in the sibling contract." He joked._

 _"Have you told her how you feel?"_

 _"There really hasn't been a good time." He frowned. "We went to the airport together when we left, and she said she'd call, but she hasn't."_

 _"Have you called her?"_

 _"Yeah. A few times." He admitted, slightly embarrassed. "I think I'm getting the message pretty clearly."_

 _"I don't think you should write her off just yet."_

 _"Write who off?" Stephen Bartowski asked as he entered the living room, Devon and Mary behind him._

 _"Oh, no one." Chuck shrugged it off._

 _"So, who's up for some pancakes?" Mary asked._

 _"Oh me, of course!" Chuck jumped up excitedly. "Devon, my mom makes the best Christmas morning pancakes, trust me."_

 _"Oh I believe you, bro. I snuck a few in already." He put his hand up for a high five._

 _"You got the first one?" Chuck asked._

 _"We saved plenty for you, son." Stephen said, noticing the pout on Chuck's face._

 _"But the first one is always the best." He said._

 _"Don't worry, I put that one aside for you." Mary whispered to him as they all filed into the dining room. Chuck grinned, appreciating his family. Christmas was his absolute favorite time of year, and he always made sure to remember every moment. But this year, he couldn't help but feel out of the loop. Looking at Ellie and Devon together, and then his parents, he wished he had someone, too. He wished he had Kate._


	3. Chapter 3

**A/N: Hello everybody! I'm really loving this story a lot. It's fun to play around with who's who and what happens with them! I changed my mind about the daughter's name, and I am going to make it significant to the story later down the line. I'm still waiting for someone to guess the women correctly, but this is only the first part of three, so I understand why no one has been right yet. I find myself writing the actual women's names sometimes, and have to catch myself or else it will give the whole thing away! Thanks for the reviews thus far, keep em' coming!**

 **-Charahfan44**

* * *

 **January 16th, 2001**

 _Chuck always hated saying goodbye to his family, but he knew he'd be back in Burbank at some point. When he got back to the Harvard campus, everything looked exactly as it had when he left. Snow covered the ground, the trees stood still, and the brick buildings kept the same darkened color. Bryce wasn't there yet, but Chuck didn't mind. He liked having the place to himself for a little bit. He sat on his bed, going over the assignments he had completed over the Christmas break. Before he knew it, he was asleep. A knock on his door woke him up a few hours later._

 _"Coming." He called groggily, getting out of bed. He opened the door, rubbing his eyes._

 _"You're here." Kate's smiling face greeted him. "I came by yesterday, but you didn't answer so I figured you were still at home."_

 _"Yeah, I just got back a few hours ago." He replied._

 _"I wanted to explain why I didn't call." She said._

 _"Don't even worry about it, I forgot you were going to anyway." He lied, trying to keep a nonchalant attitude._

 _"Oh." She looked away. "Well, my phone broke when I got off the plane. I dropped it and it broke into pieces. I got a new one once I was home, but I didn't have your number memorized so I couldn't call."_

 _"Like I said, it's cool." He smiled._

 _"Cool." She nodded, unsure of what to say next. "Well, I guess I'll see you around."_

 _"What are you doing right now?" Chuck was secretly relieved to hear that she couldn't call him, and not that she wouldn't. "I could use some food."_

 _"I could eat." She smiled._

 _"Perfect. Let me grab my coat." He rushed around the room, trying to find his shoes and winter coat. "Alright, where should we go?"_

 _"Let's just walk and see where it takes us."_

 _"Sounds good to me." He said. They walked for a bit, finding an open deli nearby. Everything else seemed to close early due to the ongoing holiday season. They agreed on the place, wanting to get inside to find warmth._

 _"So, how was home?"_

 _"Good. Warm." He replied. "My family is unlike any other. We mostly just laugh and eat so much we feel like we're going to die." He joked._

 _"Sounds fun." She said._

 _"How about you?"_

 _"It was good." Her answer was short._

 _"By all means, give me lots of details." He said sarcastically._

 _"My family isn't the greatest."_

 _"Oh, I didn't mean to-"_

 _"It's okay. I love them, don't get me wrong."_

 _"What's bad about them?"_

 _"We don't have much to talk about. My dad is a lawyer, so he asks me about being here, but that's about it."_

 _"Is that why you're studying law?"_

 _"It's what he planned for me." She nodded. Her face seemed unusually melancholy while talking about her family, so Chuck decided to change the subject. He didn't want to press her for bad memories._

 _"I'm starving, and I haven't even looked at the menu yet." He picked up the menu in front of him. "Oh, pastrami sounds incredible."_

 _"I could go for some hot chocolate." She suggested._

 _"Hot chocolate?" He looked at her._

 _"I know, I'm not twelve anymore, but it just sounds good."_

 _"Then hot chocolate you will have." He flagged down the server. "Can we get two hot chocolate's, please?"_

 _"Sure, anything else?" The server asked._

 _"Not yet." Chuck replied._

 _"Do you happen to have any nutmeg?" Kate asked._

 _"We do, actually. The holiday's aren't over yet." The server smiled._

 _"Sprinkle some of that on top." Kate smiled. The server walked away, getting them their drinks._

 _"Nutmeg?"_

 _"Trust me, it adds the magic."_

 _"I believe you." Chuck couldn't help but feel as though this was exactly where he was supposed to be._

* * *

 **PRESENT DAY**

I hated this part of the month. The part where I had to say goodbye to one of my parents for two weeks, just to go to another place to live with another. I remembered the day they told me so clearly, but it still didn't make sense. Why couldn't they talk it out and move on? Why did they have to dwell on their fighting and give up on each other?

"Did you hear me?" Dad asked, putting the last item in my lunch bag.

"Yeah, mom will pick me up after basketball." I sighed.

"I'll see you in two weeks, it'll go by fast." He noticed my mood.

"You always say that." I grumbled.

"It will get easier."

"You always say that, too."

"I know, but it's true." He handed me my lunch. "We should go or you're going to be late." We rushed out of the apartment quickly, and dad sped to the school. He dropped me off a few minutes before the first bell rang, giving me just enough time to run to class. I sat through the day, my mind focusing on everything but school. Even basketball practice seemed out of touch. I couldn't run any of the plays, and my coach noticed.

"Bartowski, come here." She yelled from the sideline. "What's going on with you today?"

"I don't know, coach. I'm not all here I guess."

"We have an important game coming up, are you going to be good for that?"

"Yeah, I'll be fine." I nodded, breathing hard.

"Start showing me something, or you'll be sitting on the bench. Got it?" She was tough, but I knew she had my back. She wasn't used to being firm with me, because I always got things done.

"I got it, coach."

"Good. Get some sleep tonight." She called practice, and like usual, mom was late picking me up. I would hide behind the gym as everyone left, because I didn't want anyone staying late to watch me. They had their own things to do, and they shouldn't have to wait because my mom was a workaholic.

"Hey, sorry I'm late." Mom drove up in her car, calling out of her window. I opened the back door, throwing my gear onto the seat. "How was your day?" She asked, watching me get into the passenger seat.

"Fine." I rested my arm on the window ledge.

"I tried getting here on time, I swear." She was genuinely apologetic.

"I know."

"So, does that mean I'm forgiven?"

"We'll see how tonight goes." I gave her a slight smile.

"I took the day off tomorrow." She stated. "I figured we could go do something fun."

"Like what?"

"I don't know, you tell me." She urged. "We can do whatever you want."

"And if I want to stay home?"

"Then we stay home."

"Why are you doing this?" I asked. It was unlike her to take a day off. "Not that I don't appreciate it."

"Because I haven't seen you in two weeks, and I want to take a step back from my job." She admitted. "Work isn't everything."

"Where's my mom, and what have you done with her?" I joked.

"I'm serious." She said. "I'm trying to be better."

"Dad's telling me the story of how you guys met." I blurted.

"What?"

"I asked him to."

"Why?"

"I don't know. I've never heard it."

"It was a completely different life back then. I mean when we met at-"

"Stop!" I cut her off. "Don't tell me anything!"

"I thought you said he was already telling you?"

"It's kind of like a game." I said. "He changed all of the names in the story, and I have to guess who you are based on what he tells me."

"That's interesting." She agreed. "What part are you on?"

"There's a woman named Kate that he met at Harvard, and he totally loved her. We stopped at the part where they get back from Christmas vacation their sophomore year, and they go out for lunch."

"Hmm. Sounds boring." She said.

"I think it's sweet." I defended him. "He was too afraid to say anything, so he showed her instead."

"That does sound like him." She laughed. I could see a flicker of nostalgia in her eyes as she spoke. "He was always a good guy."

"Yeah, except when he used another woman to make Kate jealous." I frowned. "That was pretty messed up."

"He did what?"

"Kate dated Uncle Bryce and dad was jealous, but he went out with this chick named Julia and made out with her in front of Kate to make _her_ jealous." I didn't take a breath.

"Now that doesn't sound like him."

"That's what I said!" We pulled into our driveway. I stared at the front of the house, remembering all of the times we would decorate for holiday's together, as a family.

"Well, I'm sure it's a very interesting story." She got out of the car.

"I think so."

"Has he told you about anyone else?"

"Nope, Kate's the first part."

"And do you think I'm Kate?" She asked, with a smirk.

"I don't think so. But, I have to hear about the other two serious girlfriend's before I can make my final decision." I stated. I couldn't tell if she was messing with me to throw me off, or if she was genuinely interested in the story dad was telling me. All I could do was wait and find out.

* * *

 **April 1st, 2001**

 _Chuck woke up on April Fool's day, feeling as though something had shifted. He couldn't put his finger on it, but he felt off. He felt as though something was going to happen, but he wasn't sure if it was good or bad._

 _"Dude, you've been asleep for two days. You okay?" Bryce walked up to Chuck, looking worried._

 _"What?"_

 _"I tried waking you up, and you wouldn't move. I called the paramedics, but they said you were fine." He added._

 _"I've been asleep for two whole days? I have a calculus exam that I didn't finish studying for!" Chuck got up in a flash._

 _"April Fool's!" Bryce yelled, laughing. "I changed all of the calendar's to throw you off. As smart as you are, I didn't think you'd actually believe it."_

 _"Yeah, well, I did." Chuck replied flatly. "Thanks."_

 _"Better study for that exam." Bryce winked before leaving the room. Chuck rubbed his face, feeling more stupid than he ever had before. He and Kate had been spending almost every day together, becoming better friends than he and Bryce were. It was almost ten o'clock, the time they would meet in the Barker Cafe. He struggled to get his maroon long sleeve shirt on, fearing he would be late. He showed up at ten twenty, with an amused Kate waiting for him._

 _"Rough morning?" She laughed._

 _"What?"_

 _"Your shirt's on backwards."_

 _"Oh." He felt his face turn red._

 _"I got you your favorite." She pointed to a medium black coffee and raspberry danish._

 _"Oh man, do I love you or what?" He sat down, unaware of what he had just said. He took a bite of his pastry, a smile forming on his face. "So, what are we doing today?"_

 _"Well, I don't know about you, but I have a date." She replied, causing Chuck to choke on his coffee._

 _"A date?" He asked, regaining his composure. "With who?"_

 _"A guy I met in bio."_

 _"So he's boring."_

 _"Not really. You'd think so, but he's got a great personality. He's pretty easy on the eyes too."_

 _"You and Bryce just broke up, do you think it's a good idea?" He tried changing her mind._

 _"Chuck, Bryce and I broke up almost six months ago. I think this is past due." She laughed. "Why are you trying so hard to get me not to go?"_

 _"I'm not." He coughed. "I just wanted you to think about it."_

 _"I have."_

 _"Cool." He didn't know what to say. After breakfast, they went their separate ways, each going to a different class. All Chuck could think about was Kate going out with someone else. He didn't want to ruin the friendship by saying anything, but he couldn't bear the thought of seeing her with another guy yet again. He made his way home from class slowly, taking the time to go over his decisions._

 _"What's up with you?" Bryce asked, noticing Chuck's thinking face._

 _"Nothing." Chuck shook it off._

 _"Dude. I know that face. Something's bugging you."_

 _"Can I ask you something without it being weird?" Chuck put his backpack down._

 _"Sure."_

 _"I'm kind of in love with Kate, and I want to tell her."_

 _"That was a statement." Bryce laughed. "What's the question?"_

 _"Will you hate me if I go for it?" Chuck swallowed hard._

 _"I think everyone has known since day one." Bryce said. "Hell, I'm pretty sure she knows, too."_

 _"You think so?"_

 _"Girls like guys who make the first move. She's probably just waiting for you."_

 _"So I should tell her?"_

 _"You should've told her already." Bryce shrugged. "Go, man. Before it's really too late." Chuck didn't wait to hear another word before bursting out the door and running to Kate's dorm. He was praying he would make it there before she left. He got there, out of breath, and knocked on the door._

 _"Chuck." Kate's roommate opened the door._

 _"Is Kate here?" He asked._

 _"She just left."_

 _"Where did she go?"_

 _"I don't know, she didn't tell me. I think she's going on a date?"_

 _"Great. Thanks." He turned around, walking down the hallway in defeat. He was too late. There had been so many chances for him to tell this woman how he felt, but each time he chickened out._

 _"Chuck?" The same voice he had dreamed about countless times suddenly filled his ears. He looked up to see Kate, looking more beautiful than he had ever seen before._

 _"Kate." He smiled._

 _"What are you doing in my dorm?" She asked._

 _"I wanted to talk to you." He said, moving closer. "Well, to tell you something actually."_

 _"I'm on my way out, I just forgot my wallet. Can we talk when I get back?" She tried moving past him, but he grabbed her arm lightly._

 _"It can't wait."_

 _"Is everything okay?"_

 _"Not really."_

 _"Why? What's wrong?" She looked genuinely concerned._

 _"What's wrong is that you're going out with some random guy you met in bio." He looked her straight in the eyes. "And you should be going out with me."_

 _"Chuck..." The words didn't quite compute._

 _"I know, it's too late. But maybe it doesn't have to be. You aren't gone yet."_

 _"We're friends, Chuck."_

 _"Exactly. I know you better than anyone." He replied, putting one hand on her face. "I love you."_

 _"We can't." She looked down._

 _"Why not? You can't tell me you don't feel the same way."_

 _"I-" Chuck cut her off with a kiss. A simple, soft, held back kiss. He wanted so desperately to throw her against the wall and give it everything he had, but he knew he needed to tread lightly. He pulled away, looking over every inch of her face._

 _"Tell me you didn't feel that, and I'll leave." He said. After what seemed like an eternity, she finally replied._

 _"I can't." She wrapped her arms around his neck, crashing her lips into his. At first he didn't know what was happening. But after his brain clicked, he gave the best kiss of his entire life. She was the woman of his dreams, and he finally had her._


	4. Chapter 4

**A/N: Hi guys! The updates for this story are quicker than the rest because I already know what I want to write. I'm trying my best to get my other fics updated ASAP, so keep an eye out. As for this story, I hope I'm not making things too obvious. No one has guessed correctly yet, so I think I'm doing pretty good! As always, thank you for reading and reviewing, you fans are great!**

 **-Charahfan44**

* * *

 **PRESENT DAY**

I hung up the phone with my dad that night feeling oddly happy. He had finally told me how he and Kate got together, and I was rooting for them. They seemed to genuinely care for each other, and after seeing him and my mom go through this, that's all I could hope for in a couple. I wanted to know more, but needed to go to bed. Mom and I had decided to hang out at The Grove in Burbank the next day, and I already knew I'd be tired.

"Late night?" Mom asked, noticing my tired eyes as I walked into the living room.

"Kinda." I replied.

"You still want to go out?"

"Yeah." I nodded. "Staying up was my choice, I have to live with it."

"Wise words." She laughed. "I heard you talking to someone."

"Relax, it was dad." I plopped down on the couch beside her. "He was telling me more of the story."

"You're still on that, huh?"

"I've never heard it before." I replied. "Which is pretty weird, seeing as you guys are my parents and all."

"Why is that weird?"

"Most children know how their parents met."

"Do they?"

"Yeah actually." I sassed. "And now I get to figure it out."

"You know, I actually forgot how I met your dad until you brought it up yesterday."

"Now do you remember?"

"I do." She smiled.

"Don't tell me." I reminded her. "I'm going to figure it out on my own."

"I'm kind of interested to see if you get it right." She smirked.

"Can I ask you something?"

"Always."

"Is there any possibility of you guys working things out?" I asked, wanting answers.

"I don't know." She sighed. "I'm not saying that to brush you off, either. I honestly don't know what's going to happen." She looked back to the television, not wanting to have a deep conversation so early in the morning.

"Okay." I nodded. "I'm gonna go get dressed."

"Sounds like a plan." Her normal demeanor returned. After getting dressed into my regular clothes, we spent the day out and about. One thing I loved most about my mom was that when she took the time to actually connect with me, we had the best time. I was closer with my dad, especially because he was always there, but I had a certain connection with my mom that he could never have. It wasn't something I could explain, but something I felt. We ended up going home around seven, after walking all of our problems out during the day.

"Mom?" I looked at her, peeling my eyes way from the moving palm trees outside the car.

"Yeah?"

"Thanks for taking the day off."

"Anytime." She smiled at me.

"Am I going to have to choose?" The question escaped my mouth before I could stop it.

"Choose what?"

"Between you and dad." I said. "If you guys get divorced, don't I have to pick one? Because I can't do this back and forth for the rest of my life, it's too hard."

"Whoa, no one said anything about divorce." She laughed. "We'll cross that bridge when we come to it, but for now, let's not worry about it. Okay?"

"Sure." I looked back out the window. I had a feeling this wasn't going to end the way I wanted.

"Tell me the story." Mom interrupted my thoughts.

"What?"

"I want to hear it." She said. "If I'm in it, I want to know what he's saying."

"I really don't want to be in the middle..." I trailed.

"You aren't, I promise. Just humor me."

"Okay, but if this turns out bad, I'm going to be mad at you." I warned.

"I just want to hear his side of it." She promised.

"Fine." I shrugged. "It started at Harvard, when dad literally ran into a girl named Kate."

* * *

 **April 2nd, 2001**

 _After the kiss, Chuck and Kate had sat in the hallway and talked for hours, trying to figure out how to proceed. They both agreed to take things slow, and see how each other felt. Chuck spent the night wide awake, going over every second of the kiss. The next morning, he waited in the Barker Cafe, as usual. When ten thirty hit, he figured Kate wasn't coming._

 _"Sorry I'm late." Her face was flushed as she ran smack into Chuck as he was leaving the cafe. "Are you leaving?"_

 _"I figured you weren't coming."_

 _"Why would you think that?" She asked._

 _"Yesterday, with the...you know." He mumbled._

 _"You mean when you kissed me and then we decided to date each other?" She asked playfully. "I thought we figured it out." She grabbed his hand, causing his heart to flutter._

 _"We did." He smiled. "But you're allowed to change your mind."_

 _"Do you want me to change my mind?"_

 _"Not at all."_

 _"Good." She stood on her toes, giving him a quick kiss. "Because I'm not going to." They sat in their usual spot, ordering their usual items. Chuck couldn't help but stare at Kate the entire time. He rested his elbow on the table, his chin in his hand. "What?"_

 _"What?" His hand slipped from his face._

 _"Why are you looking at me like that?" She laughed._

 _"I just can't believe this is real."_

 _"Me either."_

 _"Why can't you believe it?" He asked._

 _"Why can't you?"_

 _"Because you're totally out of my league." He explained._

 _"What makes you say that?"_

 _"Look at you." He said. "You're gorgeous, and you're going to school to become a lawyer, which means you're insanely smart. Not to mention, you can talk circles around anyone who tries to argue with you. And I'm me."_

 _"Chuck, you're more than you give yourself credit for. You won me over the moment I met you."_

 _"I did?"_

 _"I guess you just scared me."_

 _"I didn't take myself as the scary type." He joked._

 _"I mean the way you made me feel." She replied. "I didn't want to feel so much for someone."_

 _"We're in for it, aren't we?"_

 _"I think so." She reached for his hand, and he took it._

 _"So what next?"_

 _"I don't know." She frowned. "Maybe we should try a date?"_

 _"I like the sound of that." He smiled. "I'll pick you up at seven."_

 _"Seven works for me." She returned his smile. They spent another few hours together, before heading to classes. Chuck thought more clearly than he had in his entire life, blowing through every test as if it were nothing. When he got home, he explained to Bryce what had happened, and the handsome jock seemed to understand. Chuck hadn't expected his best friend to be so cool with the relationship he was starting, but Bryce surprised him. When seven hit, Chuck was standing at Kate's door, flowers in hand. He knocked confidently, fixing his hair._

 _"Wow, you look..." He looked Kate up and down, admiring the way her dress fit._

 _"Good I hope." She laughed._

 _"Incredible." He held the flowers out. "These are for you."_

 _"My favorite." She took them, placing them inside the room. "Shall we go?"_

 _"We shall."_

* * *

 **PRESENT DAY**

Two weeks always few by with each parent. The worst part was when they had to come pick me up at the others' place. The awkwardness couldn't have been worse than the moment they had to speak to each other.

"Chuck." Mom nodded, standing with the front door open.

"Hi." He avoided direct eye contact, looking to me instead. "Ready to go?"

"Uh, yeah." I stared at them both. "Oh, I forgot my backpack. I'll grab it, be right back." I went up to the top of the staircase, spying on the two below. I purposefully left them alone, hoping they'd talk to each other.

"How was it?" Dad asked.

"Fine." Mom nodded.

"Good." He scratched the back of his head.

"Yeah." She rubbed her neck. I couldn't believe how weird this was. I was so used to seeing them slow dancing in the kitchen or kissing each other or stealing glances every few minutes.

"So, uh, I'll bring her back a few days early."

"Right, you have a work thing."

"I should be back in plenty of time to pick her up on schedule."

"Just shoot me a text if you aren't."

"Sure thing."

"Great." The two shared another awkward silence. "So I heard you're telling her our story."

"Oh, she told you?"

"She's pretty excited about it."

"It is a good one." He smiled briefly. "Don't worry, I'm not making you look bad."

"I know."

"You do?"

"Well, I figured." She covered. She didn't want him to know that I was telling her what he told me. "She doesn't hate me, so that's a pretty good indication."

"Right." He laughed.

"Changing the names was pretty smart."

"I do have an incredibly big brain." He tapped his temple jokingly.

"I remember." She laughed softly.

"Got it!" I grabbed my backpack swiftly, bouncing back down the stairs. "Bye, mom." I hugged her goodbye before walking out the door.

"See you later." Dad said to her, following me down the porch steps.

"Bye." She waved. For a quick second, I thought I caught her looking at him. When we got into the car, I was ready for more.

"Okay, next part." I urged.

"I haven't even had you for a minute, slow down." He laughed.

"But I want to know what happened next!" I was antsy.

"We went on our date, and that's it."

"But I want to hear the specifics."

"I can't really give you the specifics." he replied sheepishly. "Trust me."

"Ew, dad, I'm not saying I need to know every little detail about how you spent the night. I want to know about the date. Where did you go?"

"You really are my kid, aren't you?"

"Please?" I gave him the biggest puppy dog eyes I could muster up.

"You're lucky you have your mother's eyes." On the drive back to his apartment, he told me the next part of the story.

* * *

 **April 2nd, 2001**

 _The date was the best that Chuck had ever been on. There was no better feeling in the world than being able to call your best friend your girlfriend. He and Kate talked with ease, never running out of topics. They were able to discuss life, school, and even Chuck's video game of the week. He felt so secure with her, but most of all, he felt like himself. He knew exactly who he was when he was with her._

 _"I don't feel like leaving the city, it's so perfect." Kate said. They stood hand in hand outside of the Thai restaurant in Boston, admiring their surroundings. The city was such a beautiful place, even though few people would agree._

 _"I could stay here forever." Chuck looked at her._

 _"Let's do it then."_

 _"What?"_

 _"Stay." Her eyes lit up. "We can get a hotel and spend a few days here."_

 _"Kate, we have school."_

 _"So? People skip all the time."_

 _"Me not being one of them." He reminded her._

 _"You'd rather sit in a boring lecture hall than stay in bed with me?" She asked, her eyes giving a sultry look. Chuck gulped. He hadn't thought about them sleeping in the same bed together. Of course he had imagined it, but he never thought about what it would be like if it actually happened._

 _"I'd rather get my degree." He covered._

 _"I won't let you fail." She smiled. "Come on, live a little."_

 _"Do I have a choice?"_

 _"Not really." She smirked. They grabbed a taxi, heading to a hotel in the middle of the city. Chuck wasn't sure how they could afford such a nice place, but didn't want to argue with the beautiful woman beside him._

 _"Uh, this place is a little too nice." He whispered to her, entering the building hesitantly._

 _"Chuck, I come from a family of lawyers." She smiled. "I have a little bit of money stashed away for emergencies."_

 _"This is an emergency?"_

 _"Sure." She bit her lip slightly. "You don't get to have a lot of fun, and this is a good opportunity. I consider that an emergency."_

 _"Won't your parents get mad?"_

 _"Do you not want to be with me?" She asked._

 _"What? No, why would you say that?"_

 _"Because you're trying really hard to get me to go back."_

 _"I'm just thinking logically."_

 _"Well stop." She kissed him quickly. "I'm going to get us a room." It didn't take long for her to persuade the man behind the counter to give them a bit of a discount. She had a way of charming people into doing what she wanted._

 _"Wow." Chuck took a breath as they made their way into the room. It was bigger than he had imagined. A mini bar, a king sized bed, and a marble bathroom stocked with fluffy towels and bathrobes._

 _"Incredible, right?" She fell backwards onto the bed. Chuck stood in the doorway, admiring her._

 _"You are pretty incredible." He agreed._

 _"Are you going to stand over there all night?" She asked, sitting up._

 _"I mean, I wasn't planning on all night." He joked._

 _"Chuck, get over here." She beckoned him with a finger._

 _"Right." He shut up, making his way towards her. As soon as he got close enough, she pulled him onto the bed, getting on top of him. Chuck, being the nervous wreck that he was, started rambling. "You know what I just realized?"_

 _"What?" She smiled, thinking he was about to take things to the next level._

 _"We don't have any clothes to change into." he laughed._

 _"I wasn't planning on putting anything else on once this was off." She whispered, looking down at her dress._

 _"But we need pajamas." He sat up. "This draft will be the death of us."_

 _"I'm not worried about it." She responded, crashing her lips into his._

 _"I don't know about you, but I need a good warm set of pajamas for sleeping in." He interrupted._

 _"I can be pretty warm." She said._

 _"Are you thirsty? I'm parched." Chuck got up, pushing her off._

 _"Are you okay?" She asked, genuinely confused._

 _"Fine, why?" He felt himself sweating._

 _"You're acting weird." She frowned._

 _"Me? No, I'm peachy keen." He laughed nervously._

 _"We can keep playing this game, or you can just tell me what's wrong." She got off the bed, meeting him by the mini bar. "I'm your best friend, you can talk to me."_

 _"I think that's the problem." He sighed. "I don't want to ruin our friendship. It's classic Ross and Rachel."_

 _"You're comparing us to two fictional television characters?"_

 _"Kinda." He smiled sheepishly._

 _"Chuck, we're already here." She said. "I'm already in love with you."_

 _"What?"_

 _"You heard me."_

 _"You love me?"_

 _"Of course I do, you nerd." She laughed slightly. "I've never felt this way about anyone."_

 _"Me either." He took her hands in his. "It's a lot to take in. Feelings."_

 _"I know."_

 _"I want to do this, I really do, but-"_

 _"So don't think about it." She kissed him softly. "Let it happen." She slid his jacket off smoothly, running her hands through his hair. He helped her back onto the bed, trying his best not to let the pressure get to him. He was about to sleep with the one woman he had dreamed of for over a year, and he didn't want to blow it._

 _"Kate?" He looked down at her, marveling at her beauty._

 _"Yeah?" She stroked his face with her hand._

 _"You're perfect." He smiled. Suddenly, it wasn't nerve wracking. He felt all of his emotions at once, looking down at his best friend, and it was the most amazing thing he had ever experienced._


	5. Chapter 5

**A/N: Hello again, everyone. This chapter starts with a pretty big time jump, only because I still have two other relationships of Chuck's to write about! I love this first one, but we all knew it was going to end, didn't we? Break ups are always hard to write, because sometimes they don't exactly make the most sense. I think this one in particular does, only because this is how I've written these characters. Anyway, here's the lastest installment of The Story! Hope you enjoy!**

 **-Charahfan44**

* * *

 **June 6th, 2003**

 _June of 2003 was one of Chuck's best months. He graduated with his degree in electrical engineering, while he and Kate were still going strong. They had been living together off campus for a little over a year, and had been together for a little over two. After the graduation ceremony, Chuck's family wanted to take him out for dinner. He hated leaving Kate behind, but knew she had plans with her family as well._

 _"Chuck, go. I'll be fine." She said, fixing her make up in the bathroom mirror._

 _"I know, but I still feel bad." He frowned, watching her from their bed. "Are you sure you don't want to come with me?"_

 _"I can't." She replied. "I'll see you back here tonight."_

 _"That's a long time." He whined. Kate made her way over to him, straddling him seductively._

 _"We have our own celebration to attend tonight." She whispered in his ear._

 _"A naked celebration?" He smiled like a kid on Christmas._

 _"A very naked celebration." She kissed him softly. "But right now, we have to go." She got off of him and walked into the living room._

 _"If your family gets to be too much, you are free to call me and see where I'm at." He followed her. "My parents love you."_

 _"And I love your parents." She grabbed her purse. "Make sure you tell everyone I said hi."_

 _"I will." He watched her as she left the apartment. Every time she left, he felt as though a piece of himself was going with her. He loved her so much it hurt, and he hoped he would for the rest of his life. Smiling, he made his way to the kitchen cabinet, taking out the salt. He popped off the top, and reached in, taking out a tiny square box. He had bought the ring only a few weeks before, and had planned out the perfect moment to ask. When Kate's parents decided to spend the day in Cambridge, Chuck's plans had been ruined. He sighed, unsure what his plan b would be. He put the ring back, not wanting Kate to find it, and grabbed his car keys before exiting the apartment himself._

 _"You're going to propose?" Mary Bartowski's eyes welled with tears. Chuck met up with his family at a fancy Italian restaurant in the city._

 _"That's the plan." Chuck smiled._

 _"We're proud of you, son." Stephen clapped him on the back._

 _"I know it's still pretty early, but what are your plans?" Ellie asked. "What next?"_

 _"I'd like to get a decent job." Chuck laughed. "Maybe start my own little company."_

 _"That's a good idea." Ellie nodded._

 _"And what about the wedding? When will that be?" Mary jumped right in._

 _"Mom, she hasn't even said yes yet." Chuck laughed. "That's the most important part."_

 _"She'll say yes. We've all seen the way that girl looks at you." Mary said._

 _"I agree. There's no way she'll say no." Ellie added. "Are you staying out here?"_

 _"Eventually I'd like to get back to California, but I think this is where I should stay for a while."_

 _"We support you, no matter what." Stephen said. "Just come home for Christmas, and we're good."_

 _"Always." Chuck smiled. Dinner continued to sail smoothly, each of the Bartowski's enjoying a good laugh with their meal. Chuck's phone never rang, so he assumed Kate's evening was going well too. "Well, I hate to say goodbye, but I have a woman to propose to."_

 _"You're going to do it tonight?" Ellie asked, giving her brother a hug._

 _"I can't wait." He replied. "I've waited long enough."_

 _"Go get her, son. We'll see you soon." His father hugged him next, giving a few extra pats on the back._

 _"We love you, Chuck." Mary was last. Chuck tried his best to get home quickly after dinner, but was so nervous that he ended up slowing down on purpose. He entered through the front door cautiously, his palms sweating._

 _"Kate?" He asked, noticing the empty apartment. With no response, he figured she wasn't home. This gave him extra time to get the ring and light a few candles if needed. He waited up until eleven, falling asleep on the couch. He woke up what seemed to be a few hours later, Kate sitting on the coffee table in front of him. He smiled at first, but almost immediately wiped it off his face when he noticed her holding the box crying. "I can explain."_

 _"I've been out walking." She said softly._

 _"Walking where?"_

 _"Just anywhere."_

 _"Dinner didn't go well?" He sat up and put his hands on hers, wiping her tears away with one hand._

 _"Not exactly." She looked down. "I'll never be what they expect me to be. After my sister died, everything changed."_

 _"I never know if you're okay to talk about it."_

 _"I try not to."_

 _"Did they bring it up tonight?"_

 _"No." She frowned. "I did."_

 _"Oh."_

 _"I'm tired of having so much riding on me just because she's gone."_

 _"I can't pretend to understand, because I don't. But I do know that you're right." He said._

 _"Right about what?" She asked._

 _"You'll never be what they expect you to be," He smiled, "You're better than anything they could ever imagine."_

 _"Is this what I think it is?" She asked, handing him the box._

 _"If I say yes?"_

 _"We don't have anything figured out, Chuck." She sniffed. "We don't know what comes next."_

 _"I do." He lifted her chin to catch her gaze. "I know exactly what my next move is. It's this. It's you."_

 _"How can you be sure?"_

 _"Because I love you. Kate, I love you more than I have ever loved anyone or anything. When I close my eyes and imagine my future, you're the first thing that I see. Maybe it isn't all going to be sunshine and rainbows, but if we're together, it'll be pretty damn close." He said._

 _"I love you too." She smiled. "Ask."_

 _"Really?"_

 _"Yes." She nodded. Chuck got down on one knee, popping the box open with one swift movement._

 _"Will you marry me?"_

 _"Of course." She met him on the floor, kissing him lovingly. He slipped the gorgeous diamond on her finger, causing her to stare at it. "It's beautiful."_

 _"And it's right where it belongs."_

* * *

 **PRESENT DAY**

I sat on the couch, my mouth hanging wide open. The information I had just obtained swirled around in my mind, trying to sort itself out. There was no way I'd be able to think at school.

"You proposed?" I yelled. "You were engaged?"

"Yes." Dad laughed.

"Did you marry her?"

"You'll have to wait and find out, won't you?" He got up, clearing my cereal bowl from the table.

"You can't make me wait!" I whined. "How about I take a day off of school, and you can tell me what happens next?"

"Nice try."

"Dad! You had a fiance!"

"I know, I was there." He joked.

"Are you going to finish this before I go back to mom's next week?"

"Maybe."

"Dad!"

"You better hurry up and get dressed, or you're going to be late again."

"I can be late, it's no big deal."

"Go get dressed." His voice became stern.

"Fine, but I want to hear more on the way to school." I huffed. Unlike I had requested, it didn't happen. Dad stayed tight lipped the entire time, not wanting to give me any more information before I started my day of studying. "Does something bad happen?" I asked, getting out of the car.

"What makes you ask that?"

"I don't know, I just feel like everything is too good to be true." I sighed.

"You're pretty smart." He smiled.

"Something bad does happen?"

"You'll have to find out tonight at dinner." He raised an eyebrow. "Now go to class." He nodded toward the school.

"This really isn't fair, you know." I said, shutting the door.

"No one said it would be!" He called out of the window, before driving away. The day was going to be longer than I had imagined, and it hadn't even really started yet.

* * *

 **August 11th, 2003**

 _Only two months after their engagement, everything seemed to be more smooth than normal. Chuck and Kate were more in love than they had ever been, and wedding planning was almost finished. One their days off, they spent most of their time in bed._

 _"Okay," Kate looked to her fiance, "Cake."_

 _"Is that the last thing we need?" Chuck asked._

 _"Yes. And I have a feeling we aren't going to agree." She laughed._

 _"What makes you say that?"_

 _"Because you're a chocolate guy and I'm a vanilla girl. Our taste buds are totally different when it comes to sweets. You like Snickers, and I like gummy worms."_

 _"What does that have to do with cake?" He laughed back. "You tell me your dream wedding cake, and I'll either say yes or no." He propped his head up on his pillow._

 _"Okay, fine." She sat up. "I've always wanted a three layer pineapple coconut cake with buttercream frosting. But not too much frosting, because the cake is the best part."_

 _"I can handle that." He agreed._

 _"Really?"_

 _"Let's get some chocolate fondue on the side, and you've got yourself a happy groom." He nodded._

 _"Deal." Kate got on top of him, kissing him slowly. "I can make a happy groom in some other ways, too." She whispered in his ear seductively._

 _"I think this would be the perfect time to show me exactly what you mean." His eyes lit up. Before Kate could work her magic, Chuck's phone started to ring._

 _"Don't answer that." She said._

 _"What if it's a job offer?"_

 _"Fine." She groaned. Chuck kissed her quickly before grabbing his phone and answering it._

 _"Hello?"_

 _"Is this Chuck Bartowski?"_

 _"It is."_

 _"This is Cole Barker with TechCom." The voice said. "I'm calling because we've recently come across your information, and we're looking for someone to potentially head our Burbank office."_

 _"Uh, head it?" Chuck sat up, confused._

 _"We would start you at an entry level position, but yes, you'd move up quickly. With your credentials, you'd be running it in no time." Barker replied._

 _"How long do I have to think about this?"_

 _"We'll give you until the end of the week."_

 _"Great. I'll give you a call."_

 _"We're looking forward to hearing from you." Barker hung up, and Chuck stared at his phone screen._

 _"What?" Kate asked.  
_

 _"There's a tech company that wants me to head an office." He replied, still staring at the phone._

 _"Chuck, that's great!" She said._

 _"I told them I'd think about it." He looked to her._

 _"What is there to think about?"_

 _"It's in Burbank."_

 _"California?"_

 _"Yeah."_

 _"Oh." She frowned slightly. "Well, California seems nice." She forced an enthusiastic tone._

 _"You think I should take it?"_

 _"Chuck, it's a great opportunity, and you know I'd follow you anywhere." She smiled. "I think you should at least see if it's something you want to do."_

 _"I love you, you know that?" He kissed her. "I'll call them back right now." He jumped out of bed, taking his phone with him. Kate could only imagine what kind of housewife she'd be in California, and she wasn't sure she was fully on board. After a few days had passed, Chuck had already booked his tickets to Burbank. He was going to check out the company and see if he wanted the job._

 _"Call me when you land, okay?" Kate fixed his collar as they stood at the front door._

 _"I'm only going to be gone for a few days." He assured her._

 _"I know, but still." She smiled. "Just humor me?"_

 _"Of course." He kissed her softly. "Talk to you soon." He left with a certain energy that Kate had never seen before. She already knew he was going to love the company, and that they would be moving before long. She looked around the apartment, getting an uneasy feeling. Life was about to change. Before she knew it, her phone was ringing. She searched her purse, pulling it out and answering it before the last second._

 _"Hello?"_

 _"This is Carmen Lowe from Hartford and Jones. Is this Kate?"_

 _"It is." She nodded, knowing that Carmen couldn't actually see her._

 _"We received your application, and after reviewing it, we'd like you to come in for an interview."_

 _"Me?"_

 _"I am calling you, aren't I?"_

 _"Yes." Kate was dumbstruck._

 _"How does tomorrow work for you?"_

 _"Tomorrow? Tomorrow is great." She tried keeping her excitement level low._

 _"Great. Be here at noon for an interview with the partners."_

 _"I'll be there at eleven thirty." Kate replied, realizing the other woman had hung up. She stared at her phone, just as Chuck had only a few days before. Her dreams were finally starting to happen. Then a thought hit her. They were moving to Burbank. How could she work at the top law firm in Boston when she was getting married and moving to California? Maybe she could persuade Chuck to stay? She had a decision to make, and she knew she wouldn't be able to make it lightly._

* * *

 **August 16th, 2003**

 _Kate was beyond nervous to talk to Chuck about their future together. The interview with Hartford and Jones had gone unbelievably well, and they were offering her a decent amount of money to start off as a small-case lawyer. The only problem being that this law firm was located in Massachusetts, while his new job offer came from California. When he got home, he was nothing but smiles._

 _"There she is." He walked over to the couch, giving Kate a giant kiss. "You look amazing."_

 _"I'm wearing sweats." She replied._

 _"You look great in anything." He smiled. "How's home life been?" He asked, sitting next to her._

 _"Fine." She smiled._

 _"You okay?" He asked, noticing her odd mood._

 _"Yeah, I'm great now that you're back." She snuggled into his side. "Just tired I guess."_

 _"Kate." He looked at her. "I know you better than I know myself. What's up?"_

 _"I have something to tell you." She positioned her self to face him. "I don't think you're going to like it."_

 _"Did you sleep with someone else?" He gasped, obviously joking. "Or are you pregnant?"_

 _"Chuck, this is serious." She snapped. "Sorry."_

 _"No, tell me." His attitude became somber._

 _"I got a phone call the day you left." She started. "And I didn't tell you about it because I wanted to check it out first."_

 _"What kind of phone call?"_

 _"A job offer. From a firm."_

 _"Kate, that's amazing. Why wouldn't I like that? You've worked hard to get into a firm." He said excitedly. "Your accomplishments are just as important to me as my own."_

 _"And I'm glad you think so," She looked down, "But, it's here in Boston."_

 _"Okay?"_

 _"You just went to Burbank for a job."_

 _"Right." He had forgotten all about the tech company._

 _"I'm fully prepared to follow you to California, I really am." She said._

 _"Good, because I kinda took the job." He admitted._

 _"What?"_

 _"I took it. Kate, you should see this place! It's-"_

 _"You took it already? Without talking to me?"_

 _"You just said you were prepared to come with me." He said with confusion. "What's the big deal?"_

 _"Hartford and Jones is one of the biggest law firms in America. Do you know what kind of an opportunity this is for me?" Her voice started to become louder._

 _"You mean was." He replied. "It was a big opportunity."_

 _"I haven't given them an answer yet." She folded her arms._

 _"We're moving to Burbank, it would be pretty hard to work in Boston from the other side of the country." He laughed._

 _"Maybe I'm not." She said, causing the air to stand still._

 _"How are we supposed to get married if we're in two different states?" He asked._

 _"We aren't." She said. "Maybe this is a sign."_

 _"You're kidding me, right?"_

 _"I thought that this was what I wanted, I really did. But I think now we want two completely different things, Chuck. I can't be the stay at home mom who drives places and bakes cookies. I want to be in a court room, helping save someone."_

 _"Who said anything about you staying home?"_

 _"I have an incredible opportunity here, just waiting for me. I want to take it."_

 _"Then we'll stay."_

 _"You have a job waiting for you in California. You can't stay."_

 _"I would stay for you."_

 _"But not for yourself."_

 _"That's not what I meant."_

 _"I love you, and something tells me I always will, but I can't be your wife." Kate took her ring off. "Not now."_

 _"I can't wait for you forever." He looked down as she placed the ring in his hand._

 _"And I'm not asking you to. Move on with someone who wants the same things as you. You deserve the world, Chuck Bartowski." She kissed him for the last time. "I'm going to go stay at a hotel."_

 _"You don't have to go."_

 _"If I stay, it'll just be that much harder."_

 _"Please don't go." He looked at her with complete sincerity. "I don't know what to do without you."_

 _"That's what we're going to figure out." She grabbed her coat and purse, exiting the apartment as quickly as she could. As soon as the door shut behind her, she started to cry. She knew this was the best thing for the both of them, but that didn't mean she wouldn't be hurting for the rest of her life._

* * *

 **PRESENT DAY**

Unlike before, my expression wasn't as dumbstruck. I was just plain confused at this point. How could someone so in love with another person just drop them the second something else came along? How could someone choose their job over the love of their life?

"I don't get it." I frowned.

"I didn't either, trust me." Dad replied.

"She just left you." I stated. "She got a job offer and dumped you. Who does that?"

"It took me a long time to understand why she did what she did, but I eventually did."

"Would you mind explaining it to me? Because I don't see any sense in it."

"We were barely twenty-two." He explained. "We had our whole lives ahead of us, and if we had gotten married and settled down, we wouldn't be where we are now. I wouldn't have you."

"But you loved her."

"I did, yes." He nodded. "But I got over her. I thought I needed her to be the best version of myself, and I didn't."

"I'm sorry, dad." I looked at my plate of food, setting my fork down.

"Why are you sorry?" He laughed.

"I don't know, I just feel like someone should say it for her."

"Really, I'm glad she did it."

"Seriously?" I asked.

"Yeah. I grew up because of her, and I learned something really valuable." He replied.

"Yeah? What's that?"

"I learned that the only person you can truly rely on is yourself. If you happen to find someone to confide in, that's just a plus." He smiled. "I learned a lot from my time with Kate."

"It's just so sad." I admitted. "You gave so much of your time to her. You won her over."

"Sometimes relationships are harder than they need to be." He shrugged.

"Is that what happened with mom?" I asked.

"It is." He said back.

"I don't know if I can handle the rest of the story." I sighed. "The beginning sucked."

"But you still have two more women to hear about." He raised an eyebrow. "Don't back out on me now, it's just getting interesting."

"Fine, but leave out the sad parts."

"They're all filled with sad parts." He gave me a look. "But the ending is worth it."

"How? How is it worth the heartbreak?"

"Because I have you." He smiled. "You're my happy ending."

"You wouldn't change anything?" I asked.

"Not a thing."

"Okay, fine. I'll endure the pain." I joked.

"Good. The next girl is kind of a wild card."

"Like Julia?"

"Not _that_ wild." He laughed. "But close. This girl's name was Sienna, and she was exactly what I needed." He closed his eyes for a moment, remembering the past. The way his face lit up told me that this next part of the story was going to be a good one.


	6. Chapter 6

**A/N: Hi everyone! Thank you so much to those of you who are reviewing and reading this story. There's nothing better than good feedback on a new story. Although it's a little shorter than usual, this chapter is about Chuck moving on from Kate, and I hope I made it a fun one. This next girl makes him feel like a bit of a badass, and I wanted to play around with Chuck letting out his wild side. I hope you all enjoy this next chapter as much as I do!**

 **-Charahfan44**

* * *

 **October 5th, 2003**

 _Chuck had settled into the new job quite nicely, making his way through the ranks with ease. It had only been two months, and he was already running the Burbank branch of TechCom. He had brought Morgan to the team, thinking it would be better with his best friend by his side._

 _"Dude." Morgan walked into Chuck's office, holding his cell phone in one hand. "I was just invited to the hottest party of the year."_

 _"Sounds fun, Morgan." Chuck mumbled, clicking away on his keyboard._

 _"I'm allowed a plus one." He stopped at the desk. "And my plus one is you, man."_

 _"I can't." Chuck looked up. "I have too much to do."_

 _"Can I be honest with you?" Morgan asked._

 _"No matter what my answer is to that, you're still going to do it."_

 _"You've been wallowing in self pity ever since you got back, and I get it. Your girl dumped you."_

 _"Thanks for the reminder."_

 _"You need to get out of this office, Chuck. It's changing you." Morgan gave him a look. "Let's go out and have some fun. If you hate it, we can leave."_

 _"Promise?"_

 _"Scout's honor." Morgan help up his hand in salute._

 _"Fine. Just this once." Chuck agreed. "What time?"_

 _"Ten o'clock."_

 _"Ten? That's late."_

 _"You're twenty-two, dude, not eighty." Morgan laughed. "I'll pick you up at nine thirty!" He left the office in a burst of energy. Chuck laughed slightly, shaking his head. Morgan always knew how to cheer him up. Getting ready for the party that evening, Chuck had no idea what to wear. Morgan eventually picked out a crimson button up, disregarding Chuck's protests. It wasn't the best party Chuck had ever been to, but then again, he had never partied in Beverly Hills._

 _"I'm gonna go get some air." Chuck yelled to Morgan over the loud blasting of bad pop music._

 _"I can't hear you, but okay!" Morgan yelled back, giving his best friend a thumbs up. Chuck tried going out onto the balcony, as he usually did at parties, but this one was full of people smoking and drinking. He slinked back into the house, finding an empty room to hide in._

 _"Pretty lame party, huh?" Chuck jumped as a woman emerged from under the covers of the bed. "I mean, I'd actually rather take a nap than go out there." She sighed._

 _"Uh, yeah." He nodded._

 _"Did you want one?" She asked._

 _"One what?"_

 _"A nap." She laughed, sitting up._

 _"Oh, no thanks. I don't even know who's bed this is." He replied._

 _"It's mine." She smiled. "I'd be glad to share."_

 _"This is your house?"_

 _"One of them."_

 _"It's a great party, what are you talking about?" He back-tracked. "Great music, too."_

 _"What's your name?"_

 _"Chuck Bartowski." He held out his hand._

 _"Sienna Lewis." She shook it. "And you don't have to lie. Actually, I'd prefer if you told the truth from here on out. Most people don't."_

 _"I can do that." Chuck smiled._

 _"Have you ever been to the hills before?" She stood up, going to her closet and grabbing a pair of heels._

 _"Tons of times." He replied, catching himself. "No, no I haven't."_

 _"It's not all it's cracked up to be." She stated. "I've lived here my whole life, and it's the most boring place I've ever been to."_

 _"Have you been to a lot of places?"_

 _"Twelve different countries, and all fifty states." She said proudly. "I'm still crossing more off my list."_

 _"Wow." He was genuinely intrigued. "I've never been out of the country. I grew up in Burbank, but I went to Harvard."_

 _"A smart guy, huh?" She looked at him in wonder. "Chuck, how do you feel about spontaneous adventures?"_

 _"I've never been on one." He shrugged._

 _"Would you like to?"_

 _"I mean, sure. I would like to see the Eiffel Tower at some point in my life." He rambled._

 _"Chuck," She snapped, "I can take you to see it right now."_

 _"What? You don't even know me. I could be an ax murderer."_

 _"Are you?"_

 _"No."_

 _"I trust you." She grabbed one of her many purses and opened the bedroom door. "Are you coming?"_

 _"To Paris?"_

 _"And wherever else we end up." She nodded._

 _"I don't know, I have work..."_

 _"Suit yourself." She turned to leave._

 _"Wait!" He called after her. "I'll go."_

 _"Then hurry up." with that, she was off. Chuck wasn't exactly sure who he had just met, but he knew she was going to show him the time of his life._

* * *

 **PRESENT DAY**

I was thoroughly enjoying this next part of the story. It seemed as though my dad had lived out so many adventures I had yet to learn about. He didn't strike me as the type to run away with some random girl he met at a party, but I was only just now starting to get to know him.

"So what you're saying, is that it's okay to go to Paris with a stranger who owns a private jet?" I asked, settling into my bed.

"Not at all." He warned. "In fact, if you even _think_ about it, I'm going to hunt the kid down and knock his teeth out."

"I'm sure he'll be quivering in fear." I laughed. "I like Sienna."

"Yeah?"

"She seems fun. I think she's good for you."

"Well thank you." He laughed. "It gets better."

"Duh, you get to see the Eiffel Tower!" I shouted. "You never told me you've been to Paris."

"It never came up."

"Where else did you guys go?"

"Lots of places. She really did take me around the world." He smiled.

"Did you quit your job?"

"No." He said. "I just took a lot of sick time."

"I can't believe you met a random girl and went to Paris. She could've killed you."

"I could've just as easily killed her." He shrugged. "I trusted her from the moment we met."

"Obviously." I rolled my eyes. "I don't think I would've done what you did."

"A lot of people wouldn't."

"But you did just because you trusted her?"

"It's hard to explain." He said. "There was something about her that I was drawn to."

"I don't know if I think she's mom." I frowned.

"Why's that?"

"She seems too..." I trailed.

"Easy going?"

"Slutty." I finally answered.

"Watch it." He used his dad voice.

"Sorry, I don't know how else to describe her."

"Carefree is a good word." He replied. "Sleep tight." He stood up, turning the light off as he left the room. I clicked my lamp on when he was fully out of the room, grabbing my notebook from the bedside table. Every time he told me a part of the story, I was sure to write it down. I made sure to put in every detail, looking over it each time. Before I knew it, it was already morning.

"Look who's up." Dad said as I entered the kitchen. He had the cereal ready for me.

"What time is it?"

"Almost eleven." He looked at his watch. "I figured I'd let you sleep in a bit today."

"I want to hear more." I grabbed a bowl and the cereal box, making my way to the table.

"Of course you do." He smiled. "Can't a guy eat first?"

"You can eat and tell me at the same time." I said. "Was Paris everything you imagined?"

"Pretty much." He nodded. I couldn't wait to hear more about Sienna, and figure out if she was in fact my mother. Soemthing was telling me no, but then again, what did I know? It could be anyone.

* * *

 **October 6th, 2003**

 _A straight shot to Paris only took about nine hours in a private jet. With a connecting commercial flight, they would've been there in twelve. On their way, Sienna told Chuck about her life. He got a few words in, but he really just loved to listen to her talk. She had so many incredible stories to tell, and he wanted_

 _"So, we have to see the Tower." She said as they touched down on the tarmac. "What else?"_

 _"I've never had a true french baguette." He shrugged._

 _"Alright, we'll get some food too." She laughed. "We also have to ride a gondola on the riviera. It's beautiful." She smiled._

 _"How many times have you been here?"_

 _"A few." She said modestly. They stepped off the plane slowly, and the air hit Chuck like a wall. It was clean, and even the sky seemed more blue than normal. Sienna's driver got them into the city in no time, and they went straight to the Eiffel Tower. "Well, this is it." Sienna did a Vanna White movement with her arms, and Chuck's jaw dropped._

 _"It's incredible." He gasped. "And big."_

 _"It's pretty from up top."_

 _"Uh, I like looking at it from below." He coughed._

 _"Don't tell me you're afraid of heights!" She joked._

 _"Of course not." His tone wasn't believable._

 _"Oh my god, you totally are." She laughed._

 _"It's not funny, I have a traumatizing experience." He whined. "Not my fondest memory."_

 _"Okay, okay. We can stay down here." She backed off. "Let's go get lunch and come back here for a picnic." She suggested, grabbing his hand._

 _"I could still be an ax murderer." He said._

 _"As many times as you've brought it up, I still don't believe it." She rolled her eyes. "You could've easily killed me on the plane."_

 _"That is true."_

 _"So, what's your story?" She asked._

 _"Uh, what?" Chuck was distracted by the beautiful scenery around him. "Sorry."_

 _"I should know better than to start the deep conversations in Paris." She joked._

 _"No, it's perfect." He smiled. "I don't really have much of a story." He shrugged._

 _"Everyone has a story."_

 _"I'm from Burbank, I went to Harvard, and now I'm back in California, practically running a tech company."_

 _"Why didn't you stay in Boston?"_

 _"It wasn't for me." He didn't want to talk about Kate._

 _"Oh, please," She rolled her eyes, "Nobody leaves Boston for Burbank without a good reason."_

 _"You really want to know?" He asked._

 _"Desperately." She smiled._

 _"I was dumped."_

 _"I figured." She said. "You've got a sad look permanently attached to your face."_

 _"Do I really?"_

 _"That's why I brought you here. And why I'm going to take you to a ton of other places. There's nothing better than traveling the world after a huge break up, trust me."_

 _"How do you know it was huge?"_

 _"Again, the face."_

 _"Right."_

 _"I'm going to ask you something right here and now." She stopped in front of him. "I want you to be completely honest."_

 _"Okay." He nodded._

 _"Are you ready to get over Kate?"_

 _"What?"_

 _"Are you prepared to move on?" She asked. "You have to be open to forgetting about her, or my plan will never work."_

 _"What plan?"_

 _"My plan to seduce you and show you my world." She said with a slight smirk._

 _"I'm ready to move on. One hundred percent."_

 _"Good." With one swift movement, she grabbed his face, pulling him in for a kiss. It was unlike anything he had ever experienced. There was nothing tender about it, and he liked it. This kiss was so full of energy and passion, unlike he had ever known._

 _"Wow." He breathed as she pulled away._

 _"That's what I'm going to show you." She winked. With that, she walked ahead, a little bounce in her step. Chuck shook his head slowly, following her to the cafe. He was only starting to realize what he had gotten himself into._


	7. Chapter 7

**A/N: Hey all! Sorry this chapter has taken so long. I have a SERIOUS case of writers block with all of my stories, and I'm trying to lift the psychological rock blocking my brain. I promise I will update as quickly as I can, but I'm also graduating college at the end of the month, and things are getting crazy. Just bear with me. I love you all! Enjoy this chapter of one of my favorites :)**

 **-Charahfan44**

* * *

 ** _October 17th, 2003_**

 _Chuck was used to working long days, especially after Barker quit the company. Chuck was twenty-three years old, and already the owner of a multi-million-dollar tech company. The days went by fast, sometimes even causing him to forget what day it was._

 _"Howdy, stranger." Sienna's voice at the doorway made Chuck look up from his paperwork._

 _"What are you doing here?" He asked._

 _"Wow, what a welcome." She laughed. "Did you forget we had plans?"_

 _"Oh, uh, of course not." He tried to sneak a peek at his calendar._

 _"Dinner reservations at six." She walked up to his desk, closing the calendar. "It's now seven."_

 _"I am so sorry." He rubbed his face in his hands. "Work has me on overdrive." He sighed._

 _"I figured." She smiled. "So, I brought dinner to you." With a snap of her fingers, four waiters stepped into the office, bringing trays of food with them._

 _"What?" He looked up at her._

 _"I bought the restaurant for the evening." She smiled. "Isn't money just great?"_

 _"I-I don't know what to say." Chuck stammered._

 _"Say you'll turn off that computer and eat with me." She held out her hand._

 _"I have a lot to do here..." He trailed._

 _"Wrong answer." She smiled once more. "Come on, Chuck, live a little."_

 _"I guess I will." He smiled back._

 _"Still not what I'm looking for."_

 _"Of course I will." He replied, taking her hand. They ate a full three course meal, starting with elegant salads followed by premium steaks, and an apple crumble for dessert. "I can't possibly eat another bite." Chuck dropped his fork on the plate, sitting back sluggishly._

 _"Good?"_

 _"Fantastic." He smiled at her. "I'm sorry I've been so M.I.A lately."_

 _"I get it, you're busy."_

 _"I'm not too busy for my beautiful girlfriend." He said, trying to charm her. "I promise we'll get away as soon as I'm done with this software update proposal."_

 _"I don't know what that means, but okay." She laughed. "I'm thinking Maui."_

 _"A trip?"_

 _"You said 'getaway'."_

 _"I meant from the office." He replied._

 _"Chuck, I own a private jet. Might as well use it." She joked._

 _"I don't know if I can go anywhere right now. Would you settle for a nice movie night on my couch?"_

 _"We've been doing that." She whined. "Remember when we talked about me showing you the world?"_

 _"Hawaii is in the US." He laughed._

 _"Okay fine, let's go to Greece."_

 _"Sienna…" He trailed. "I like you a lot, but I have a lot of work to do."_

 _"I get it."_

 _"You've never worked a day in your life, how would you get it?" He replied, unaware of what he had just said._

 _"That's what you think of me?" She stood up._

 _"What? No, that's not what I meant."_

 _"Sure it is."_

 _"Running a business is hard enough, but doing it all alone is worse."_

 _"Sure."_

 _"Sienna." He grabbed her wrist. "I love you."_

 _"What?"_

 _"I love you, and I think you're amazing." He kissed her softly. He wasn't quite sure why he said it, but he needed to say something to make up for his comments._

 _"I love you too." She smiled, hugging him._

 _"So, am I forgiven?"_

 _"Only if you say yes to Greece." She looked up at him with big brown eyes._

 _"Yes."_

 _"Really?"_

 _"I could use a vacation."_

 _"You're the best." She kissed him, putting all she had into it. In that moment, everything felt off. Chuck stood there, holding his girlfriend, thinking of Kate._

* * *

 **Present Day**

Dad and I made a tradition of visiting a Go-Kart track every month, in order to keep some fun. Even when he was the busiest, he still made time to race me on the track. I didn't really understand at first, but soon realized that he wanted to have something for us to have as "ours". Even when he and mom were together, she would never tag along.

"Wait, I don't get it." I frowned, putting on my helmet.

"What?"

"You didn't love Sienna, but you told her you did anyway?"

"Yeah." He shrugged.

"Why?"

"I don't really know. I mean, I thought I was going to have those feelings for her at some point."

"But you weren't over Kate yet."

"No, I wasn't."

"That's pretty messed up, dad." I said.

"I know. Just goes to show you that you shouldn't say something that important unless you mean it." He explained. "Life throws plenty of curve balls at you, and sometimes you just can't dodge getting hit."

"But sometimes you can get yourself out of the game entirely. That way there's no chance of the ball coming anywhere near you." I replied.

"When did you get so smart?"

"Mom asks me the same thing." I laughed. "I'm just growing up, I guess."

"You guess? You're practically eighty."

"I wouldn't go that far." I rolled my eyes. "I'm just saying, you could've broken up with her."

"I did eventually."

"Yeah, but I mean right then and there. She sounds like she was becoming too needy."

"She could be your mother." He raised an eyebrow.

"She doesn't sound like mom."

"You don't think so?" He asked. The expression on his face was throwing me off.

"Are you admitting that she is?"

"I'll tell you more after the race." He made sure our helmets were firmly placed over our heads, and we got into our cars. I always made sure to get the red one, because it had better drifting power. I won without much of a battle, and I knew dad was going all out.

"Ha! That's number five." I said excitedly, taking my helmet off.

"Yeah, yeah." He shook his head, doing the same. "You down for some nachos?"

"Always." I replied. We ate slowly, enjoying the day together. "So, after you told Sienna that you loved her, what happened?"

"You just can't wait, can you?" He laughed.

"It's hard. There's so much to figure out!"

"So you do think she's your mom?"

"I don't know now."

"That's the point." He laughed.

"Why can't you just skip to the end?"

"I can't tell you all at once, where's the fun in that?"

"I thought it would've been easier."

"Oh yeah?"

"I thought I would know who she was right away."

"We've only gotten through two women."

"So you and Sienna broke up right after that?"

"Not exactly."

"Dad!" I whined. "You're killing me!"

"It's complicated." He looked at his plate.

"I know."

"There's a difference between knowing and understanding." He looked up at me. "I need you to understand."

"So continue and I will." I nodded.

"Okay, let's see..."

* * *

 ** _October 20th, 2003_**

 _Only a few days had passed since Chuck had blurted the three most coveted words in any relationship, and already Sienna was taking everything to a whole new level. She constantly sent him messages, and booked trips through to the next year._

 _"So, next year we're going to the Maldives." Sienna was in bed next to Chuck, on her brand new Apple laptop._

 _"Uh, sounds nice." He forced a smile._

 _"Sounds nice?" She looked away from the computer. "It sounds amazing."_

 _"Right." He nodded slightly._

 _"Are you okay?"_

 _"Fine. Just tired."_

 _"Chuck, I know when you're tired." She shut her laptop. "And this isn't it. Talk to me."_

 _"I just think maybe all of this is moving really fast."_

 _"You're the one who said you loved me."_

 _"I know, but-"_

 _"But what?" She cut him off._

 _"Nothing."_

 _"No, please, say it." She folded her arms._

 _"I think we should take a few days to get our heads straight."_

 _"A few days apart?"_

 _"Yeah."_

 _"You're breaking up with me?" Her voice cracked._

 _"No, it's not like that at all." He tried to cover it up. "I just have a lot going on, and I don't want you to think I'm blowing you off."_

 _"You should've started with that." She said softly._

 _"I know, I'm sorry." He kissed her quickly. "I'm an idiot."_

 _"Thank you for admitting it." She smiled slyly._

 _"Keep looking at those tickets, and I'll call you tomorrow." He pushed the covers off the bed and climbed out._

 _"What? Where are you going?"_

 _"If you only want it to be a few days, I have to get started now."_

 _"You can't stay one night?"_

 _"If I stay, we both know I won't leave tomorrow." He pulled his shirt over his head. "It'll go by quick, I promise." He walked over to her, giving her one final kiss before leaving. He drove to the office, wanting to get some work done before the day was completely over. He didn't see any cars in the parking lot when he pulled up, but noticed an office light on as he walked into the building._

 _"Hey, Mick." He greeted his head security guard. "Is someone here?"_

 _"The new gal." The gruff man responded._

 _"Amelia?"_

 _"Sure."_

 _"Thanks." Chuck nodded, walking over to the elevator and stepping inside. He pressed 25, and waited until the elevator stopped. He stepped out, loving the quiet sound he heard._

 _"Mr. Bartowski." The brunette came around the corner, colliding into Chuck._

 _"Amelia." He coughed._

 _"Sorry." She looked down at the papers she dropped. "I didn't realize anyone else was here."_

 _"I just got here." He smiled, helping her pick up her things. "You know, you don't have to be here this late, you're already hired."_

 _"I know." She laughed. "I get more things done when it's quiet."_

 _"I know exactly what you mean."_

 _"Besides, I have a lot to catch up on."_

 _"That you do."_

 _"I think the new software update is a bad idea." She blurted._

 _"What?" Chuck hadn't been expecting a comment like that. "You are talking about the one we're releasing in five days, right?"_

 _"I know it's almost ready to launch, but I think we need to hold off. On the test runs, there have been major problems. Bugs, freezing issues, and crashes we can't afford."_

 _"So what do you suggest we do?"_

 _"Get our techs on it, and upgrade it."_

 _"Upgrade the first version?"_

 _"I get it, it sounds crazy." She pushed her glasses back into position on her face. "But I know what I'm talking about. You hired me as your chief software designer for a reason."_

 _"Your contract technically doesn't start until this download is finished."_

 _"I know."_

 _"I'll go over the numbers and re-evaluate my decision." He scratched his forehead._

 _"That's all I'm asking." She nodded. "I'll see you tomorrow." With that, she was off. Chuck sighed, making his way to his office. He knew that work had taken over his life, and he wasn't quite sure how to stop it._

* * *

 **Present Day**

"Have fun?" Mom met us at the front door of the house. She seemed to be extra happy today, and I didn't want to know why.

"Yeah, I beat him bad." I laughed, looking at my dad.

"See you in a few weeks." He gave me a kiss on my head before I entered the house.

"I have a favor to ask." She stopped dad before he could leave.

"Uh, sure."

"I'm going to be out of town next week, and I was hoping you could watch her."

"That shouldn't be a problem." He nodded.

"I didn't know you had a trip," I added. "It wasn't on the calendar."

"It's a spur of the moment thing." She shot me a look. "Thanks."

"I'll see you next week then." He smiled at me once more before mom closed the door.

"You just had to say something." She rolled her eyes at me playfully.

"Where are you going this time? Australia?"

"It's not a work thing." Her voice was quiet. She quickly made her way into the kitchen, trying to avoid me. But I was her daughter, and I attacked things head on.

"What do you mean?"

"It's not for work. It's personal."

"You're with someone?" I stopped walking. I'm pretty sure she sensed it, because she stopped too.

"It's not like that." She frowned, unable to keep eye contact. "It's not serious."

"I don't understand."

"I know."

"You can't."

"I am."

"But what about dad?" I asked.

"Dad and I are separated."

"But technically you're still married." I snapped back.

"Not for much longer." The words left her mouth before she could catch herself.

"What?"

"I shouldn't have said that..." She trailed.

"But you did, and now you get to explain." I demanded.

"We were going to tell you together."

"Tell me what?" I could feel the lump in my throat rising.

"We aren't getting back together." She made sure to look me in the eyes this time. "We just recently talked about it, and we decided together."

"And how long were you going to wait to tell me?" The tears rolled down my face without warning.

"Not very long, I promise." She extended a hand out to me, but I refused it. "Don't shut me out."

"Why? You shut me out." I spat.

"That's not what's happening, and you know it. You can be mad all you want, but we are going to discuss this together as a family."

"No we aren't. You're going to run off with a stranger and leave us here." I didn't know what I was saying at this point.

"Come here." She opened both arms. "That wasn't a suggestion." I sulked over to her, letting her wrap her arms around me. She held me for a few minutes, letting me cry it all out.

"I don't hate you."

"Well thanks for that." She let out a small laugh, releasing me. "I hope that you never hate me."

"I don't think I could." I wiped my face.

"Good." She smiled, pushing my hair back. "You know you can always talk to me. About anything."

"I know." I hugged her again, not wanting to let go.


	8. Chapter 8

**A/N: Hello everyone! Sorry this update has taken me a little while, I was working on finishing up Coma. This chapter focuses on a new lady in Chuck's life, but is she the mother? I know that I focused on Kate for a long time, and Sienna is already getting phased out, but it's for a reason. I like the dynamic between Chuck and Amelia, only because she's on his level! Anyway, hope you enjoy this next chapter!**

 **-Charahfan44**

* * *

Present Day

I had a tough time falling asleep, mostly because I kept thinking about my mom and dad. Why couldn't they work things out? I knew plenty of people whose parents were divorced, but now that I was going through it with my own, I didn't quite know how to handle it. Mom was up before me the next morning, making waffles for breakfast.

"Sleep okay?" She asked, pouring batter into the griddle.

"Not really." I grumbled.

"I figured." She replied guiltily. "Do you want to talk yet?"

"Not really." I repeated myself.

"I talked to dad." She said. "When he comes to pick you up in a few weeks, we're going to talk together."

"Okay."

"Hey," She looked up at me, "I love you, and I'm sorry."

"People get divorced." I shrugged. "It's life."

"Doesn't mean it isn't hard."

"Yeah." I sighed. "Did you want to get back together?" I asked.

"What?"

"Did you want to work it out?"

"A part of me did." She nodded. "But an even bigger part knew that our problems are too big for what I want, versus what I need." I watched her face change as she spoke. She started off normal, as though she was explaining something simple. But as she thought about what she was saying, I saw the sadness fill her eyes. It was something I would never forget.

"I'm sorry." I said.

"For what?"

"Asking."

"You're entitled to questions." She smiled. "It affects you too."

"But it's pretty heavy."

"Just a little." She kept a light attitude. "How many waffles do you want?"

"Three."

"Are you growing again?"

"Probably." I laughed.

"Oh, I forgot to tell you yesterday, I have to go into the office later." She put my waffle on a plate, handing it to me carefully.

"That's fine." I replied, taking a bite.

"Are you sure? You're free to come with."

"Is that your way of saying I have to?"

"I'd rather not leave you here alone." She said.

"It's fine." I nodded.

"We won't be there long, I promise."

"As long as you don't try to explain work things to me, I'll be fine." I joked. "Your job is so boring."

"My job is incredibly difficult." She replied. "And exciting. You've never been in a-"

"See? You haven't even started talking about it and I'm already bored." I faked a yawn. She shook her head at me, laughing.

"Fine, think what you want." She put her hands up in defeat. "But one day you'll appreciate what I do."

* * *

 _October 21st, 2003_

 _Amelia's first day on the job was a hectic one. One of the newest software designers had accidentally deleted the schematics for the new update, and it had everyone in a frenzy._

 _"Tell me exactly what you did." Chuck stood over the IT genius' computer._

 _"I don't know, Mr. Bartowski. It just went away." He stammered._

 _"Things don't just 'go away'." Amelia scoffed. "You must've hit the wrong button."_

 _"I swear I didn't." The guy looked like he was about to cry._

 _"Okay, let me see if I can work some magic." Chuck offered. "Move." The guy got out of his seat, allowing Chuck to take over._

 _"Maybe if you hack into the system and tear down the firewall, you can find a back up." Amelia offered. "That's what I would do."_

 _"I've got it." Chuck said._

 _"Right." Amelia backed off just a hair. After twenty minutes of intense hacking and searching, Chuck managed to salvage his software update._

 _"Bingo." He clicked on the recovered file, sitting back in his chair with triumph._

 _"You know what you're doing." Amelia smiled._

 _"Of course, I can't run a software company without knowing how to work the software." He chuckled. "If I'm not better than my employees, then what am I doing running this company?"_

 _"Most bosses don't think that way."_

 _"I'm not like most bosses."_

 _"That's for sure." She said. Chuck noticed a hint of flirtation in her eyes, which made him get up._

 _"Uh, you can oversee the rest of the job, right?" He asked. "I have some things to go take care of."_

 _"Sure thing." She nodded._

 _"Great." He turned to his worker. "Try not to screw it up this time, huh?"_

 _"I'm not fired?" The guy asked._

 _"We all make mistakes. Just learn from it and don't do it again." Chuck clapped him on the shoulder, easing his worry. He walked out of the room, and ventured to his office. He checked his phone once he was there, and noticed six missed calls from Sienna._

 _"You went pretty easy on him." Amelia stood in the doorway._

 _"I thought you were going to watch him?"_

 _"He should be fired." Her arms were folded._

 _"That's ultimately my call."_

 _"You're the boss, Chuck. If you let people get away with things, they'll keep doing it."_

 _"The only thing is, what he did was an accident."_

 _"If you say so." She walked up to his desk. "We should talk about this new update."_

 _"What about it?"_

 _"We should be charging more."_

 _"You like to insert yourself, don't you?" He laughed. "I think it's fine the way it is."_

 _"We can triple the worth of this company, but you need to start taking risks."_

 _"And if those risks put our people out of jobs? Or crash our stocks?" Chuck asked. "I'm not a risk taker because I like stability."_

 _"You hired me, because I'm good at what I do," She looked directly into his eyes, "So let me do what I'm best at."_

 _"Amelia, I like you." Chuck started. "But I don't trust you yet."_

 _"Fair enough." She shrugged. "But you will."_

 _"That sounds like a threat." He joked._

 _"Maybe it is." She looked back over her shoulder before leaving his office completely. He wasn't quite sure what to do with her, but he knew she was going to be a handful._

 _"Mr. Bartowski, your girlfriend is on line one." Chuck's assistant rang him over the com system._

 _"Thank you." He pushed a button, replying. He picked up the phone slowly, tired of having to constantly please his girlfriend. "Hey, Sienna." He answered, trying to sound cheerful._

 _"Hey, babe." Was her reply. "You busy?"_

 _"I'm always busy." He sighed. "But never too busy for you. What's up?"_

 _"I'm planning a vacation."_

 _"Of course." He let out a small laugh. "Where?"_

 _"I don't know yet. But I do know that you need a vacation." She said. "So, you pick. Wherever you want to go, we'll make it happen."_

 _"I really can't travel right now. I thought we talked about this?"_

 _"We had a brief discussion."_

 _"And apparently you weren't listening."_

 _"I was listening, I'm just trying to do something nice for you."_

 _"And I appreciate that, but I have to stay here and work. The second I have time off, you'll know about it."_

 _"Fine." She couldn't hide her irritation. "Am I going to see you tonight?"_

 _"I have to work late." He replied._

 _"I guess I'll see you when I see you then."_

 _"Soon, I promise." Without another word, the line went dead._

* * *

Present Day

I wasn't a huge fan of mom's office building. It smelled like old wood and uptight adults. Her office was one of the first ones to the left when you stepped off the elevator on the tenth floor, and I knew it made her feel important. There were only five other people on her floor, one of whom was working today.

"Good morning." The man stepped out of his office.

"Morning." Mom replied.

"I didn't expect to see you here." He said. "Last minute business?"

"Yeah, I forgot to file a few things." She gave him a weird look, thinking I wouldn't catch it. I frowned slightly, trying to figure out what it meant.

"Well, I'm sure you've got a lot to do." He smiled. I didn't like this guy.

"Will you go put this in my office?" Mom handed me her purse. "I'll be right there." I didn't argue. When I opened her door, I tried listening in to their conversation from the inside.

"Did your ex agree to taking her a week early?" He asked.

"Yes, we're good to go." Mom's voice shifted.

"I'm a little nervous."

"Why?" She sounded like a school girl. "It's just a trip."

"I haven't taken a trip since my wife died." He admitted. "Not to make this depressing or anything."

"No, I get it. I haven't either." Mom replied.

"If I had known that you'd be here with her, I would've stayed home." He changed the conversation. "I know it must be a little weird."

"It's fine, really."

"Well, I'll see you soon."

"Definitely." She replied. I peered around the corner to see him give her a quick kiss, and it made my stomach turn. How long had mom been seeing this jerk? She wasn't even divorced yet! Before she turned around, I popped back into her office, pretending to look at my phone. "Sorry, had to go over a few things with him while he was here."

"I've never seen him before, is he new?" I played it off, but inside I was dying.

"He's been here for about six months. Good guy." She kept it short.

"Seems like a tool." I mumbled.

"What?" She hadn't heard me.

"Oh nothing." I kept my focus on my phone screen.

"How's the story going?" Mom changed the subject.

"Good. He's telling me about his second girlfriend right now, the one after Kate."

"The one who took him to Paris?" She asked, typing away on her computer.

"You know about that?" I asked.

"Of course I do, I married him." She laughed. "It's not some big secret."

"Right." I said. "Well, I definitely don't think you're Sienna."

"I'm not." She winked.

"Is that supposed to throw me off?"

"Who knows." She shrugged.

"It's killing me." I said. "I want him to just tell me already. But I started it, so I guess I have to wait."

"I guess you do."

"If I paid you one hundred dollars right now, would you tell me?"

"You don't have a hundred dollars." She laughed again.

"But if I did?"

"Not a chance."

* * *

 _October 21st, 2003_

 _Chuck couldn't focus at work. He was restless, and he didn't want to be stuck in the office anymore. He wanted to be on a tropical island with his girlfriend, but things were starting to stall with her._

 _"You're still here?" Amelia's voice cut through his thoughts._

 _"I'm always here." He put his face in his hands. "I could say the same for you."_

 _"I'm leaving." She held up her purse. "You should, too. Don't you have a girlfriend?"_

 _"I'm starting to think I don't." The further away he drifted, the harder she clung to him._

 _"You should have some fun."_

 _"When?" He pointed to all of the papers on his desk._

 _"I don't know, make time." She shrugged. "Spending all of your time here is going to drive you insane."_

 _"You're probably right."_

 _"Probably?" She let out a small laugh. "Have you ever been laser tagging?"_

 _"What?"_

 _"Laser tag. It's a game-"_

 _"I know what it is, I just haven't heard anyone mention it since I was like twelve." He giggled. "Are you suggesting I take time out of my night to play a child's game?"_

 _"Maybe."_

 _"Maybe I would say yes."_

 _"Maybe or definitely?"_

 _"Definitely. Let's go." He stood up._

 _"That's the spirit." She smiled, causing Chuck to smile back. He walked over to his coat rack, grabbing his jacket, and following her out. They ended up going to a mini golf course, because the laser tag arena was closed. After a few minutes in, he realized that this could be viewed as something more than it really was, so he kept small talk. His plan was to keep his head down and try to keep his distance._

 _"Are you okay?" His plan hadn't worked._

 _"Yeah, why?" He replied._

 _"Because you've barely said a word to me since we got here." She said._

 _"I'm just in my head."_

 _"We came here to get you out of your head." She gave him a look._

 _"Right."_

 _"Maybe you should hire a co-CEO." She suggested. "This work load is too much for one person to handle."_

 _"I know. But I feel like it's my responsibility to keep it afloat, you know?"_

 _"I do." She nodded. "Just don't let it take its toll on you."_

 _"I'm trying not to."_

 _"Seems to be working out great." She kept the light mood._

 _"Thank you." Chuck blurted._

 _"For?" Amelia hit her ball into the hole._

 _"Bringing me here." Chuck replied._

 _"I'm not always so harsh." She said._

 _"I figured." He smiled. "I like this version."_

 _"Me too, but she doesn't come around too often."_

 _"We should change that." He hit his ball next. "Like a weekly thing."_

 _"I could agree to that."_

 _"Just something to help us get away from the office for an hour or two."_

 _"I'm two steps ahead of you."_

 _"Oh yeah?"_

 _"I may know a place." She said._

 _"Does it involve golf?"_

 _"Not exactly."_

 _"Should I be afraid?"_

 _"Not exactly." She replied with a smile. "You'll be on your way to trusting me, that's for sure."_

 _"I'm sorry about that." He looked down._

 _"It's okay."_

 _"But we're pretty much partners now. I should trust you." He looked at her. "So, from here on out, I do."_

 _"Well I appreciate that." She let out a small laugh. "Let's see how far we can go from here." She turned to hit her golf ball once more. Chuck couldn't help but stare at her. In this outdoor night lighting, she looked like the most beautiful woman in the world._


	9. Chapter 9

**A/N: Hi everybody! Sorry about the wait for the next chapters of my stories. I'm working six days a week now that I've graduated college, and life always seems to get in the way. Thank you to everyone who has commented or read thus far, I appreciate you all so much. I hope you enjoy this next chapter of The Story! Keep guessing... ;)**

 **-Charahfan44**

* * *

 ** _November 14th, 2003_**

 _Chuck paced back and forth in his apartment. He hated doing things like this, but it had to be done. He had to break up with Sienna. They had just come back from a trip to Cancun, and he knew that they were going in separate directions. She was exactly what he needed to get over Kate, but now he was fully moved on. He rubbed his hands together nervously, and stopped dead in his tracks when he heard a knock on the door. He gulped, walking up to the door hesitantly._

 _"Miss me already?" Sienna's face was vibrant and rested._

 _"I'm glad you're here." He forced a smile, accepting a quick kiss from her._

 _"Of course I'm here." She smiled back, entering the apartment. "Besides, I have a surprise for you." She took her coat off and placed it on the rack beside the door._

 _"For me?" He asked._

 _"Yes, for you. You've been working so hard lately." She sat on the couch, while Chuck stood beside it. "Sit." She tapped the pillow next to her. He slwoly sat beside her, becoming more nervous than before._

 _"You really didn't have to-" He stopped short when she pulled a small box out of her purse._

 _"Open it." She said excitedly._

 _"What's in it?"_

 _"Open it and find out, silly." She laughed. "I can't just tell you, that wouldn't be any fun."_

 _"Look, Sienna..." Chuck trailed._

 _"Before you put your foot in your mouth, just open it." She gave him a look. He scratched his head, giving her a small laugh. After a few more seconds of staring at it, he opened the box slowly._

 _"It's a key." He pulled the gold object out out of the box. "To your place I'm assuming?"_

 _"I want you to move in." She put a hand on his leg. "This place is really boring." She joked._

 _"Sienna, I called you over here so that we could talk."_

 _"About?" She looked at him with an oblivious expression._

 _"About where this is going." He looked down at his hands._

 _"Were you going to ask me to move in here?" She laughed._

 _"Not exactly." He looked back up at her._

 _"I'm confused."_

 _"I know, I'm not really explaining this." He took a breath. "I think we're going down different paths."_

 _"What do you mean?"_

 _"When we first got together I was all about traveling and seeing things I never had before, but now I have a business to run and I can't keep dropping my responsibilities for play time."_

 _"Wow." She replied. "I'm just play time?"_

 _"That's not what I meant." He back tracked. "I just mean that you have all the time in the world to explore and venture out-"_

 _"And not work." She crossed her arms._

 _"Again, not what I meant." He said._

 _"You know what, Chuck? You're afraid of commitment."_

 _"I don't think that's it."_

 _"You might not think so, but I know it. We had something real, here, and you just blew it." Sienna stood up, grabbing the key out of Chuck's hand. "When you change your mind, you can call me, but I'm not going to wait forever." She stormed out of the apartment, leaving Chuck speechless. After a few hours, he made his way to the office, where he spent most of his evenings._

 _"Don't you have an apartment?" Amelia was in her office when she noticed Chuck walk by the doorway._

 _"Uh, yeah." He nodded._

 _"You look like crap." She laughed. "Rough night?"_

 _"Rough couple of hours." He leaned against the door frame. "Didn't you say something about a date tonight?"_

 _"He listens." She smiled. "I had a date, but I cancelled it. Too many documents to look through." She pointed at her computer screen._

 _"I most definitely would've let you go through those tomorrow." He replied._

 _"I wasn't that excited." She shrugged. "How's Sienna?"_

 _"We broke up."_

 _"Oh." Without hesitating, she pulled a bottle of scotch out of her desk drawer. "I like to use this for rainy days."_

 _"Honestly, this isn't a rainy day for me." He said. "I feel free."_

 _"Not the relationship type?" Amelia poured two glasses while Chuck made his way to the chair in front of her desk._

 _"Not the Sienna type." He replied, accepting a glass._

 _"So why be with her in the first place?"_

 _"I don't want to sound like an ass, but she helped me move on from my ex."_

 _"Ah. The rebound girlfriend." Amelia nodded._

 _"I had feelings for Sienna, don't get me wrong. I can't just use someone like that." He explained. "It's just that..." He tried to find the right words to explain his reasoning._

 _"You needed something new and exciting."_

 _"Exactly." He took a swig._

 _"I understand completely. Us women use men the same way." She smiled. "I hate the double standard."_

 _"Thank you." He smiled back._

 _"So now what? You're going to work yourself to death?"_

 _"That was the plan, yeah." He joked. "I'm not going to focus so much on women, that's for sure."_

 _"That's too bad." Amelia looked at him with big eyes. "Sorry, I don't know why I said that." She blushed, looking down._

 _"I didn't really mind it." Chuck set his glass down on her desk, leaning closer. "Not to be too forward, but you're a big reason why I broke up with Sienna."_

 _"What happened to you not focusing on women?"_

 _"I said women plural. Doesn't mean I wasn't going to ficus on one in particular." He was leaning on the desk, their faces only inches apart._

 _"This could get messy." She whispered._

 _"I don't care." He pushed her hair behind her ear. "There's just something about you, Amelia." Before he knew it, their lips were touching. Everything about her warmth drew him in. They pulled apart, breathing heavily._

 _"We should probably do some work." Amelia finally said._

 _"Probably." Chuck nodded. But instead, they crashed together once more, not caring about anything else in the world but each other._

* * *

Present Day

I loved grocery trips with dad. He always let me get exactly what I wanted, within reason of course. Mom was a health nut, but dad knew how to give a kid a sugar rush.

"So, your broke up with Sienna and immediately started kissing Amelia?" I asked, looking at the cereal aisle.

"Kind of." He replied.

"Kind of? You just told me that exact thing."

"I know." He cringed. "There's more to it than that, though. It's hard to explain adult things to a kid."

"Yeah, well, you already started so you may as well suck it up and give it to me straight." I replied.

"You have got to stop growing up." He laughed.

"What are the odds?" A voice behind us made us turn around.

"Mom!" I ran over to her, giving her a hug.

"Trip over so soon?" Dad asked, joining us.

"Yeah." Her answer was short. "Reese's Puffs, really?" She looked inside the cart.

"You know me." Dad shrugged.

"That I do." She smiled.

"You can totally shop with us, we're just getting started." I blurted. "Unless you're done or whatever."

"You mind?" She looked to dad, making sure that the awkwardness wouldn't be too heavy.

"No, feel free." He said. I knew he was doing it for me, and I appreciated him for it.

"So how's school?" Mom asked me.

"Oh you know, I'm getting all A's." Dad replied.

"Ha ha." Mom gave him a playful look. "And how about you?" She looked to me.

"Same old same old." I laughed.

"Just about time for soccer season, huh?"

"Yeah."

"I have her bulking up for tryouts." Dad chimed in.

"I can see that." Mom looked at the cart once more. "Lots of carbs and sugar should do just fine."

"I'm thinking I'm going to switch to goalie this year." I announced. "Now that I'm one of the tallest on the team, I have more of a shot."

"That's true, you did sprout right up." Dad put a hand on my head. "I can kick some balls at your face and see how you do if you want." He smirked.

"That's exactly what I want." I rolled my eyes. "Actually, mom, I was hoping you could help. I know you played in high school." I looked to her.

"Gosh, it's been forever." She said. "But I will help you as much as I can." She nodded.

"How's work?" Dad asked.

"The same." Mom replied. "I have a big client coming in this week and I don't know that I'm all that prepared for it."

"Why's that?" He asked.

"Probably because I took too much time off."

"A week. You took a week off." He laughed. At this point, I was walking behind them, watching them converse. It was rare that they got along, and I wasn't about to interrupt.

"You know how it is, Mr. CEO." She smacked him, laughing back.

"True. But vacations are well deserved on our parts." He said.

"Well, I should probably get going. I only have an hour until I need to get into the office." Mom stopped walking. I could tell she was starting to feel too comfortable around dad.

"Yeah, we're just about done." He agreed.

"I'll see you next week, okay?" She turned to look at me.

"Sure." I smiled. I watched as she walked away, and a part of me noticed some hesitation. I thought I saw a glimpse of the same look she'd give him when I was younger. A look of love.

"So, how about we get some ice cream?"

"Afraid to do it in front of her, are you?" I laughed.

"One-hundred percent." He smiled back at me.

"Back to the story." I changed subjects. "I want to know what happened with Amelia."

"A lot happened with Amelia." He sighed.

"Good or bad?"

"Both, really." He said. "I loved her a lot."

"More than Kate?"

"I've never loved anyone more than I loved Kate." He said without hesitation. "I can safely say that I still haven't met a woman quite like her." The way his eyes sparkled when he said her name made me reflect back on Kate's part of the story. Could woman number one be my mother? I was going to have to wait and find out.

* * *

 ** _December 23rd, 2003_**

 _Christmastime came faster than Chuck had wanted, but he made sure he was prepared for the holiday. He spared no expense in decorating the office, and made sure to put presents for everyone under the tree._

 _"Santa, is that you?" Amelia's voice caused him to jump._

 _"You scared the crap out of me!" He said._

 _"Sorry, I heard a noise and thought I'd come check it out." She laughed. "Are those real presents?"_

 _"They sure aren't fake." He walked up to her._

 _"You're such a good boss." She kissed him softly, putting her arms around his neck. "We don't deserve you."_

 _"I know." He smiled, kissing her back. "Now, your present I couldn't put under there."_

 _"Oh really?"_

 _"Really."_

 _"So do I get it later?" She asked._

 _"Possibly."_

 _"Mr. Bartowski," One of the techs walked into the room, causing Chuck and Amelia to jump apart, "I have the stats you asked for."_

 _"Right. I forgot you were still here." Chuck coughed. "You're good to go, enjoy your holiday."_

 _"Thank you, sir." He gave the two a weird look before leaving the room._

 _"You forgot?" Amelia looked at Chuck._

 _"I still think we should stop hiding this."_

 _"Chuck, we've already had this conversation. It would make things really difficult."_

 _"More difficult than sneaking around and barely getting time together?" He asked. "Who cares that we're dating?"_

 _"I wouldn't really say we're dating." Amelia replied._

 _"What?" This caused Chuck to frown. "What is this then?"_

 _"I don't know, I'm having fun."_

 _"Fun? That's all this is to you? Fun?"_

 _"Look, this is why I didn't want to say anything. Office romances get messy."_

 _"This is only getting messy because you seem to think all we're doing is having 'fun'." Chuck used air-quotes. "I have legitimate feelings for you, Amelia, and you obviously don't feel the same way."_

 _"I like you." She said._

 _"Apparently not enough."_

 _"Can we forget that this conversation ever happened and go back to how it was twenty minutes ago?" She asked. "I think you're reading too much into this."_

 _"Fine." Chuck looked down._

 _"Are you sure?"_

 _"Yeah." He couldn't meet her eyes. "I have a few more things to go grab. I'll call you later." He gave her a quick kiss before leaving the building. He walked around the block, looking at all of the buildings in the city. He had true feelings for this girl, and they had only started dating a few months before. Already he felt as though it wasn't going to last, and he wasn't quite sure what to do about it._

 _"Chuck?" A voice from in front of him made Chuck look up. Standing in front of him was none other than Kate._

 _"Kate?" He asked, dumbfounded._

 _"Is this the biggest coincidence you've ever encountered or what?" She laughed. Her laugh caused Chuck to melt a little bit inside. It was something he'd never thought he'd hear again._

 _"Yeah, mostly because you live in Boston." He replied._

 _"I'm out here for work." She explained. "I'm really close to making partner at the firm."_

 _"That's amazing." He smiled. "I'm really happy for you."_

 _"What about you?" She asked. "How've you been?"_

 _"Well, I took over the company and I'm still technically single. So, pretty much the same."_

 _"Technically?"_

 _"It's a long story."_

 _"You look different." She blurted._

 _"I have been using a new shampoo." He joked._

 _"No, I don't mean physically. You look sad, Chuck." She gave him a caring look. "I know I don't really have the right to say this, but you shouldn't be with someone who makes you feel like this."_

 _"You don't know how I feel." He replied. "And you're right, you don't get to say things like that to me."_

 _"I'm sorry how I left things." She looked away. "I shouldn't have done that to you."_

 _"You don't say." He scoffed. "Sorry."_

 _"Don't be. I hurt you." She looked up. "All I know is that you're an amazing person and you deserve to be happy. Don't let anyone make you feel less than that. Promise me."  
_

 _"I promise." He nodded._

 _"Maybe it was good that we ran into each other on a random street." She laughed. "Take care of yourself, Chuck. And tell that girl how you really feel."_

 _"You too." He gave her a slight smile before walking away. He had finally gotten the closure he needed to move on, and he felt completely free. He made his way back to the office quickly, hoping that Amelia was still there._

 _"Back so soon?" She had just finished locking her office door when he exited the elevator._

 _"Yes." He breathed heavily._

 _"Did you run?"_

 _"Sort of."_

 _"Why?"_

 _"Because this isn't just fun, and you know it. I felt it the moment we met, Amelia. There's something real here, but for some reason you don't want to admit it."_

 _"Chuck-"_

 _"No. I'm not going to let you convince yourself that this is less than it is."_

 _"I was engaged." She said. "Before I moved here, I was engaged."_

 _"Oh."_

 _"He died."_

 _"I didn't-"_

 _"I don't like to tell people because they look at me the same way you're looking at me now." She explained. "I do think that we have something, but I'm just not ready to explore it full on. I need more time."_

 _"I can definitely give you time." He nodded. "I'm sorry I just assumed..."_

 _"It's okay, I should've told you." She sighed. "I'm learning to deal with it."_

 _"You shouldn't have to." He rubbed her shoulder. "Can I take you home?"_

 _"Of course." She smiled. "You're a really good guy, Chuck."_

 _"I try." They walked out of the office together, and Chuck couldn't help but feel guilty. Sienna had helped him get over Kate, but now he had to wait for the perfect woman to move on from the love of her life. He was prepared to wait as long as he had to._


End file.
